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class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Physical properties</span> </div> </a> <ul id="toc-Physical_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Chemistry</span> </div> </a> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Productions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Productions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Productions</span> </div> </a> <ul id="toc-Productions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Natural_occurrences_of_the_phenanthrene_derivatives" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Natural_occurrences_of_the_phenanthrene_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Natural occurrences of the phenanthrene derivatives</span> </div> </a> <button aria-controls="toc-Natural_occurrences_of_the_phenanthrene_derivatives-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Natural occurrences of the phenanthrene derivatives subsection</span> </button> <ul id="toc-Natural_occurrences_of_the_phenanthrene_derivatives-sublist" class="vector-toc-list"> <li id="toc-In_plants" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_plants"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>In plants</span> </div> </a> <ul id="toc-In_plants-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Phenanthrene</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 37 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-37" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">37 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%8A%D9%86%D8%A7%D9%86%D8%AB%D8%B1%D9%8A%D9%86" title="فينانثرين – Arabic" lang="ar" hreflang="ar" data-title="فينانثرين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Fenantren" title="Fenantren – Azerbaijani" lang="az" hreflang="az" data-title="Fenantren" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%81%D9%86%D8%A7%D9%86%D8%AA%D8%B1%D9%86" title="فنانترن – South Azerbaijani" lang="azb" hreflang="azb" data-title="فنانترن" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B0%D0%BD%D1%82%D1%80%D1%8D%D0%BD" title="Фенантрэн – Belarusian" lang="be" hreflang="be" data-title="Фенантрэн" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Fenantr%C3%A8" title="Fenantrè – Catalan" lang="ca" hreflang="ca" data-title="Fenantrè" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Fenanthren" title="Fenanthren – Czech" lang="cs" hreflang="cs" data-title="Fenanthren" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phenanthren" title="Phenanthren – German" lang="de" hreflang="de" data-title="Phenanthren" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A6%CE%B1%CE%B9%CE%BD%CE%B1%CE%BD%CE%B8%CF%81%CE%AD%CE%BD%CE%B9%CE%BF" title="Φαινανθρένιο – Greek" lang="el" hreflang="el" data-title="Φαινανθρένιο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Fenantreno" title="Fenantreno – Spanish" lang="es" hreflang="es" data-title="Fenantreno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Fenantreno" title="Fenantreno – Esperanto" lang="eo" hreflang="eo" data-title="Fenantreno" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Fenantreno" title="Fenantreno – Basque" lang="eu" hreflang="eu" data-title="Fenantreno" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D9%86%D8%A7%D9%86%D8%AA%D8%B1%D9%86" title="فنانترن – Persian" lang="fa" hreflang="fa" data-title="فنانترن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Ph%C3%A9nanthr%C3%A8ne" title="Phénanthrène – French" lang="fr" hreflang="fr" data-title="Phénanthrène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Feanaintr%C3%A9in" title="Feanaintréin – Irish" lang="ga" hreflang="ga" data-title="Feanaintréin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8E%98%EB%82%9C%ED%8A%B8%EB%A0%8C" title="페난트렌 – Korean" lang="ko" hreflang="ko" data-title="페난트렌" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Fenantrena" title="Fenantrena – Indonesian" lang="id" hreflang="id" data-title="Fenantrena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Fenantrene" title="Fenantrene – Italian" lang="it" hreflang="it" data-title="Fenantrene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%AB%E0%B3%80%E0%B2%A8%E0%B2%BE%E0%B2%82%E0%B2%A5%E0%B3%8D%E0%B2%B0%E0%B2%BF%E0%B2%A8%E0%B3%8D" title="ಫೀನಾಂಥ್ರಿನ್ – Kannada" lang="kn" hreflang="kn" data-title="ಫೀನಾಂಥ್ರಿನ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Fenantr%C4%93ns" title="Fenantrēns – Latvian" lang="lv" hreflang="lv" data-title="Fenantrēns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Fenantr%C3%A9n" title="Fenantrén – Hungarian" lang="hu" hreflang="hu" data-title="Fenantrén" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B0%D0%BD%D1%82%D1%80%D0%B5%D0%BD" title="Фенантрен – Macedonian" lang="mk" hreflang="mk" data-title="Фенантрен" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fenantreen" title="Fenantreen – Dutch" lang="nl" hreflang="nl" data-title="Fenantreen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%82%A7%E3%83%8A%E3%83%B3%E3%83%88%E3%83%AC%E3%83%B3" title="フェナントレン – Japanese" lang="ja" hreflang="ja" data-title="フェナントレン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Fenantren" title="Fenantren – Polish" lang="pl" hreflang="pl" data-title="Fenantren" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Fenantreno" title="Fenantreno – Portuguese" lang="pt" hreflang="pt" data-title="Fenantreno" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Fenantren" title="Fenantren – Romanian" lang="ro" hreflang="ro" data-title="Fenantren" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B0%D0%BD%D1%82%D1%80%D0%B5%D0%BD" title="Фенантрен – Russian" lang="ru" hreflang="ru" data-title="Фенантрен" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Fenantren" title="Fenantren – Slovenian" lang="sl" hreflang="sl" data-title="Fenantren" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Fenantren" title="Fenantren – Serbian" lang="sr" hreflang="sr" data-title="Fenantren" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Fenantren" title="Fenantren – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Fenantren" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Fenantreeni" title="Fenantreeni – Finnish" lang="fi" hreflang="fi" data-title="Fenantreeni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Fenantren" title="Fenantren – Swedish" lang="sv" hreflang="sv" data-title="Fenantren" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%9F%E0%B8%B5%E0%B9%81%E0%B8%99%E0%B8%99%E0%B8%97%E0%B8%A3%E0%B8%B5%E0%B8%99" title="ฟีแนนทรีน – Thai" lang="th" hreflang="th" data-title="ฟีแนนทรีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B0%D0%BD%D1%82%D1%80%D0%B5%D0%BD" title="Фенантрен – Ukrainian" lang="uk" hreflang="uk" data-title="Фенантрен" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Phenanthrene" title="Phenanthrene – Vietnamese" lang="vi" hreflang="vi" data-title="Phenanthrene" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%8F%B2" title="菲 – Wu" lang="wuu" hreflang="wuu" data-title="菲" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8F%B2" title="菲 – Chinese" lang="zh" hreflang="zh" data-title="菲" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q422037#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Phenanthrene" title="View the content page [c]" 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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Polycyclic aromatic hydrocarbon composed of three fused benzene rings</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Phenanthrene </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Phenanthrene-numbering.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Phenanthrene-numbering.svg/180px-Phenanthrene-numbering.svg.png" decoding="async" width="180" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Phenanthrene-numbering.svg/270px-Phenanthrene-numbering.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Phenanthrene-numbering.svg/360px-Phenanthrene-numbering.svg.png 2x" data-file-width="827" data-file-height="480" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Phenanthrene_molecule_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the phenanthrene molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Phenanthrene_molecule_ball.png/180px-Phenanthrene_molecule_ball.png" decoding="async" width="180" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Phenanthrene_molecule_ball.png/270px-Phenanthrene_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/Phenanthrene_molecule_ball.png/360px-Phenanthrene_molecule_ball.png 2x" data-file-width="2000" data-file-height="1295" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Phenanthrene_C14H10.JPG" class="mw-file-description" title="Phenanthrene"><img alt="Phenanthrene" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Phenanthrene_C14H10.JPG/220px-Phenanthrene_C14H10.JPG" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Phenanthrene_C14H10.JPG/330px-Phenanthrene_C14H10.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Phenanthrene_C14H10.JPG/440px-Phenanthrene_C14H10.JPG 2x" data-file-width="5152" data-file-height="3864" /></a><figcaption>Phenanthrene</figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Phenanthrene</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=85-01-8">85-01-8</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C1%3DCC%3DC2C%28%3DC1%29C%3DCC3%3DCC%3DCC%3DC32">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1905428 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=28851">CHEBI:28851</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.970.html">970</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.001.437">100.001.437</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q422037#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>266-028-2</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>28699 </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C11422">C11422</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=C031181">C031181</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/995">995</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/448J8E5BST">448J8E5BST</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID6024254">DTXSID6024254</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q422037#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YNPNZTXNASCQKK-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YNPNZTXNASCQKK-UHFFFAOYAC</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C1=CC=C2C(=C1)C=CC3=CC=CC=C32</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>14</sub><span title="Hydrogen">H</span><sub>10</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002178234000000000♠"></span>178.234</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless solid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.18 g/cm<sup>3</sup><sup id="cite_ref-GESTIS_1-0" class="reference"><a href="#cite_note-GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>101 °C (214 °F; 374 K)<sup id="cite_ref-GESTIS_1-2" class="reference"><a href="#cite_note-GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>332 °C (630 °F; 605 K)<sup id="cite_ref-GESTIS_1-3" class="reference"><a href="#cite_note-GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>1.6 mg/L<sup id="cite_ref-GESTIS_1-1" class="reference"><a href="#cite_note-GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−127.9·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_811dcee2cbfc5fb2" /></span><map name="ImageMap_811dcee2cbfc5fb2"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>171 °C (340 °F; 444 K)<sup id="cite_ref-GESTIS_1-4" class="reference"><a href="#cite_note-GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_symmetry" title="Molecular symmetry">Point group</a></div> </td> <td>C<sub>2v</sub><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>0 <a href="/wiki/Debye" title="Debye">D</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=444046459&page2=Phenanthrene">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Phenanthrene</b> is a <a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">polycyclic aromatic hydrocarbon</a> (PAH) with formula C<sub>14</sub>H<sub>10</sub>, consisting of three fused <a href="/wiki/Benzene" title="Benzene">benzene</a> rings. It is a colorless, crystal-like solid, but can also appear yellow. Phenanthrene is used to make dyes, plastics, pesticides, explosives, and drugs. It has also been used to make bile acids, cholesterol and steroids.<sup id="cite_ref-factsheet_3-0" class="reference"><a href="#cite_note-factsheet-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Phenanthrene occurs naturally and also is a man-made chemical. Commonly, humans are exposed to phenanthrene through inhalation of cigarette smoke, but there are many routes of exposure. Animal studies have shown that phenanthrene is a potential carcinogen.<sup id="cite_ref-factsheet_3-1" class="reference"><a href="#cite_note-factsheet-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> However, according to IARC, it is not identified as a probable, possible or confirmed human carcinogen.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Phenanthrene's three fused rings are angled as in the <a href="/wiki/Phenacene" title="Phenacene">phenacenes</a>, rather than straight as in the <a href="/wiki/Acene" title="Acene">acenes</a>. The compounds with a phenanthrene skeleton but with nitrogen atoms in place of CH sites are known as <a href="/wiki/Phenanthroline" class="mw-redirect" title="Phenanthroline">phenanthrolines</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History_and_etymology">History and etymology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenanthrene&action=edit&section=1" title="Edit section: History and etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenanthrene was discovered in <a href="/wiki/Coal_tar" title="Coal tar">coal tar</a> in 1872 independently by <a href="/wiki/Carl_Graebe" title="Carl Graebe">Carl Graebe</a> (article manuscript received on November 1st<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>) as well as by <a href="/wiki/Wilhelm_Rudolph_Fittig" title="Wilhelm Rudolph Fittig">Wilhelm Rudolph Fittig</a> and his doctoral student <a href="/w/index.php?title=Eugen_Ostermayer&action=edit&redlink=1" class="new" title="Eugen Ostermayer (page does not exist)">Eugen Ostermayer</a><span class="noprint" style="font-size:85%; font-style: normal;"> [<a href="https://de.wikipedia.org/wiki/Eugen_Ostermayer" class="extiw" title="de:Eugen Ostermayer">de</a>]</span> (manuscript received on November 19th<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> but Ostermayer's dissertation defended in August<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>). Fittig and Ostermayer were able to determine the structure of the compound by oxidizing it first to a <a href="/wiki/Phenanthrenequinone" title="Phenanthrenequinone">corresponding quinone</a> and then to <a href="/wiki/Diphenic_acid" title="Diphenic acid">diphenic acid</a>, and soon Graebe confirmed it by a synthesis from <a href="/wiki/(Z)-Stilbene" title="(Z)-Stilbene">stilbene</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Prior to February 1873 Fittig sent a letter to Graebe where he proposed to name the hydrocarbon phenanthrene (<a href="/wiki/German_language" title="German language">German</a>: <i lang="de">Phenanthren</i>) in order to account for its similarity to <a href="/wiki/Biphenyl" title="Biphenyl">biphenyl</a> and <a href="/wiki/Anthracene" title="Anthracene">anthracene</a>, which was swiftly adopted.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Physical_properties">Physical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenanthrene&action=edit&section=2" title="Edit section: Physical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenanthrene is nearly insoluble in water but is soluble in most low-polarity organic solvents such as <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">carbon tetrachloride</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> and <a href="/wiki/Benzene" title="Benzene">benzene</a>. </p><p>Phenanthrene is fluorescent under ultraviolet light, exhibiting a large <a href="/wiki/Stokes_shift" title="Stokes shift">Stoke shift</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It can be used in <a href="/wiki/Scintillator" title="Scintillator">scintillators</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenanthrene&action=edit&section=3" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Reactions of phenanthrene typically occur at the 9 and 10 positions, including: </p> <ul><li><a href="/wiki/Organic_oxidation" class="mw-redirect" title="Organic oxidation">Oxidation</a> with <a href="/wiki/Chromic_acid" title="Chromic acid">chromic acid</a> gives gives <a href="/wiki/Phenanthrenequinone" title="Phenanthrenequinone">phenanthrenequinone</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Organic_reduction" class="mw-redirect" title="Organic reduction">Organic reduction</a> to 9,10-dihydrophenanthrene with <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> gas and <a href="/wiki/Raney_nickel" title="Raney nickel">raney nickel</a><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Electrophilic_halogenation" title="Electrophilic halogenation">Electrophilic halogenation</a> to 9-bromophenanthrene with <a href="/wiki/Bromine" title="Bromine">bromine</a><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Aromatic_sulfonation" title="Aromatic sulfonation">Aromatic sulfonation</a> to 2 and 3-phenanthrenesulfonic acids with <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a> to diphenylaldehyde<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Productions">Productions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenanthrene&action=edit&section=4" title="Edit section: Productions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenanthrene is extracted from coal tar, where it comprises 5% by weight.<sup id="cite_ref-Ullmann_16-0" class="reference"><a href="#cite_note-Ullmann-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>In principle it could be obtained by chemical synthesis. The <b>Bardhan–Sengupta phenanthrene synthesis</b> is a classic way to make phenanthrenes.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Bardhan-SenguptaPhenanthreneSynthesis.png" class="mw-file-description" title="Bardhan–Senguptam phenanthrene synthesis"><img alt="Bardhan–Senguptam phenanthrene synthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Bardhan-SenguptaPhenanthreneSynthesis.png/480px-Bardhan-SenguptaPhenanthreneSynthesis.png" decoding="async" width="480" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Bardhan-SenguptaPhenanthreneSynthesis.png/720px-Bardhan-SenguptaPhenanthreneSynthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Bardhan-SenguptaPhenanthreneSynthesis.png/960px-Bardhan-SenguptaPhenanthreneSynthesis.png 2x" data-file-width="1286" data-file-height="256" /></a></span></dd></dl> <p>This process involves <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitution</a> using a tethered <a href="/wiki/Cyclohexanol" title="Cyclohexanol">cyclohexanol</a> group using <a href="/wiki/Diphosphorus_pentoxide" class="mw-redirect" title="Diphosphorus pentoxide">diphosphorus pentoxide</a>, which closes the central ring onto an existing aromatic ring. <a href="/wiki/Dehydrogenation" title="Dehydrogenation">Dehydrogenation</a> using <a href="/wiki/Selenium" title="Selenium">selenium</a> <a href="/wiki/Aromatizes" class="mw-redirect" title="Aromatizes">aromatizes</a> the other rings into aromatic ones as well. The aromatization of six-membered rings produces <a href="/wiki/Hydrogen_selenide" title="Hydrogen selenide">H<sub>2</sub>Se</a>. </p><p> Phenanthrene can also be obtained photochemically from certain <a href="/wiki/Diarylethene" title="Diarylethene">diarylethenes</a> (<a href="/wiki/Mallory_reaction" title="Mallory reaction">Mallory reaction</a>):</p><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Scheme_7_Rev.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Scheme_7_Rev.png/220px-Scheme_7_Rev.png" decoding="async" width="220" height="159" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Scheme_7_Rev.png/330px-Scheme_7_Rev.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Scheme_7_Rev.png/440px-Scheme_7_Rev.png 2x" data-file-width="1452" data-file-height="1048" /></a><figcaption></figcaption></figure><p> Other synthesis routes include the <a href="/wiki/Haworth_reaction" class="mw-redirect" title="Haworth reaction">Haworth reaction</a> and the <a href="/wiki/Wagner-Meerwein_rearrangement" class="mw-redirect" title="Wagner-Meerwein rearrangement">Wagner-Meerwein</a>-type <a href="/wiki/Ring_expansion_and_contraction" title="Ring expansion and contraction">ring-expansion</a>, as depicted below: </p><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:StilAlt.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/StilAlt.png/220px-StilAlt.png" decoding="async" width="220" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/StilAlt.png/330px-StilAlt.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/StilAlt.png/440px-StilAlt.png 2x" data-file-width="783" data-file-height="263" /></a><figcaption></figcaption></figure><p>Commercially phenanthrene is not synthesized but extracted from the byproducts of coal coking, since it makes around 4–6% of <a href="/wiki/Coke_oven" class="mw-redirect" title="Coke oven">coke oven</a> coal tar.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><div class="mw-heading mw-heading2"><h2 id="Natural_occurrences_of_the_phenanthrene_derivatives">Natural occurrences of the phenanthrene derivatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenanthrene&action=edit&section=5" title="Edit section: Natural occurrences of the phenanthrene derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Morphinan.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Morphinan.svg/120px-Morphinan.svg.png" decoding="async" width="120" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Morphinan.svg/180px-Morphinan.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Morphinan.svg/240px-Morphinan.svg.png 2x" data-file-width="172" data-file-height="210" /></a><figcaption>Structure of morphinan, which features a partially reduced phenanthroline core</figcaption></figure> <p><a href="/wiki/Morphinan" title="Morphinan">Morphinan</a> is the <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a> found in several <a href="/wiki/Psychoactive_drug" title="Psychoactive drug">psychoactive drugs</a>, consisting of <a href="/wiki/Opiate" title="Opiate">opiate</a> <a href="/wiki/Analgesic" title="Analgesic">analgesics</a>, <a href="/wiki/Cough_suppressant" class="mw-redirect" title="Cough suppressant">cough suppressants</a>, and <a href="/wiki/Dissociative_drug" class="mw-redirect" title="Dissociative drug">dissociative</a> <a href="/wiki/Hallucinogen" title="Hallucinogen">hallucinogens</a>, among others. Examples <a href="/wiki/Morphine" title="Morphine">morphine</a>, <a href="/wiki/Codeine" title="Codeine">codeine</a>, and <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a> (DXM).<sup id="cite_ref-Ullmann_16-1" class="reference"><a href="#cite_note-Ullmann-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p><a href="/w/index.php?title=Ravatite&action=edit&redlink=1" class="new" title="Ravatite (page does not exist)">Ravatite</a> is a natural mineral consisting of phenanthrene.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> It is found in small amounts among a few coal burning sites. Ravatite represents a small group of organic minerals. </p> <div class="mw-heading mw-heading3"><h3 id="In_plants">In plants</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenanthrene&action=edit&section=6" title="Edit section: In plants"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Phenanthrenes" class="mw-redirect" title="Phenanthrenes">Phenanthrenes</a></div><p>Phenanthrene derivatives occur in plants as <a href="/wiki/Phenanthrenoid" title="Phenanthrenoid">phenanthrenoids</a>. They have been reported from flowering plants, mainly in the family <a href="/wiki/Orchidaceae" class="mw-redirect" title="Orchidaceae">Orchidaceae</a>, and a few in the families <a href="/wiki/Dioscoreaceae" title="Dioscoreaceae">Dioscoreaceae</a>, <a href="/wiki/Combretaceae" title="Combretaceae">Combretaceae</a> and <a href="/wiki/Betulaceae" title="Betulaceae">Betulaceae</a>, as well as in the lower plant class <a href="/wiki/Marchantiophyta" title="Marchantiophyta">Marchantiophyta</a> (liverworts).<sup id="cite_ref-Kovacs_20-0" class="reference"><a href="#cite_note-Kovacs-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenanthrene&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/1,10-Phenanthroline" title="1,10-Phenanthroline">Phenanthroline</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenanthrene&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-GESTIS-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-GESTIS_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GESTIS_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-GESTIS_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-GESTIS_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-GESTIS_1-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=022900&lang=en">Record of CAS RN <i>85-01-8</i></a> in the <a href="/wiki/GESTIS_Substance_Database" title="GESTIS Substance Database">GESTIS Substance Database</a> of the <a href="/wiki/Institute_for_Occupational_Safety_and_Health_of_the_German_Social_Accident_Insurance" title="Institute for Occupational Safety and Health of the German Social Accident Insurance">Institute for Occupational Safety and Health</a> </span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">Peter Atkins, J. D. P., Atkins' Physical Chemistry. Oxford: 2010. P. 443.</span> </li> <li id="cite_note-factsheet-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-factsheet_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-factsheet_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://archive.epa.gov/epawaste/hazard/wastemin/web/pdf/phenanth.pdf">"Phenanthrene Fact Sheet"</a> <span class="cs1-format">(PDF)</span>. <i>archive.epa.gov</i>. U.S. Environmental Protection Agency<span class="reference-accessdate">. Retrieved <span class="nowrap">19 July</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=archive.epa.gov&rft.atitle=Phenanthrene+Fact+Sheet&rft_id=https%3A%2F%2Farchive.epa.gov%2Fepawaste%2Fhazard%2Fwastemin%2Fweb%2Fpdf%2Fphenanth.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenanthrene" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/aldrich/p11409">"Phenanthrene"</a>. <i>Sigma-Alrdich</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Sigma-Alrdich&rft.atitle=Phenanthrene&rft_id=https%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2Fp11409&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenanthrene" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGraebe1872" class="citation journal cs1">Graebe, C. 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(1872). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=cwaLZrjMd0oC&pg=PA933">"Ueber einen neuen Kohlenwasserstoff aus dem Steinkohlentheer"</a>. <i>Berichte der deutschen chemischen Gesellschaft</i>. <b>5</b> (2): <span class="nowrap">933–</span>937. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.187200502100">10.1002/cber.187200502100</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0365-9496">0365-9496</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+deutschen+chemischen+Gesellschaft&rft.atitle=Ueber+einen+neuen+Kohlenwasserstoff+aus+dem+Steinkohlentheer&rft.volume=5&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E933-%3C%2Fspan%3E937&rft.date=1872&rft_id=info%3Adoi%2F10.1002%2Fcber.187200502100&rft.issn=0365-9496&rft.aulast=Ostermayer&rft.aufirst=E.&rft.au=Fittig%2C+R.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DcwaLZrjMd0oC%26pg%3DPA933&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenanthrene" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOstermayer1872" class="citation book cs1 cs1-prop-foreign-lang-source">Ostermayer, Eugen (1872). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=K5NTAAAAcAAJ"><i>Ueber einen neuen Kohlenwasserstoff im Steinkohlentheeröl: Inaugural-Dissertation</i></a> (in German). 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Vol. 5, <a rel="nofollow" class="external text" href="http://www.orgsynth.org/orgsyn/pdfs/CV5P0489.pdf">p. 489</a> (1973); Vol. 41, p. 41 (1961).</span> </li> <li id="cite_note-Ullmann-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_16-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchmidtGriesbaumBehrBiedenkapp2014" class="citation book cs1">Schmidt, Roland; Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2014). 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"Natural phenanthrenes and their biological activity". <i>Phytochemistry</i>. <b>69</b> (5): <span class="nowrap">1084–</span>1110. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2008PChem..69.1084K">2008PChem..69.1084K</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.phytochem.2007.12.005">10.1016/j.phytochem.2007.12.005</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18243254">18243254</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Phytochemistry&rft.atitle=Natural+phenanthrenes+and+their+biological+activity&rft.volume=69&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1084-%3C%2Fspan%3E1110&rft.date=2008&rft_id=info%3Apmid%2F18243254&rft_id=info%3Adoi%2F10.1016%2Fj.phytochem.2007.12.005&rft_id=info%3Abibcode%2F2008PChem..69.1084K&rft.aulast=Kov%C3%A1cs&rft.aufirst=Adri%C3%A1na&rft.au=Vasas%2C+Andrea&rft.au=Hohmann%2C+Judit&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenanthrene" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenanthrene&action=edit&section=9" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" 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class="navbox-group" style="width:1%;background:azzurro;">Saturated<br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="AlkanesCnH2n_+_2135" scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkane" title="Alkane">Alkanes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> + 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Ethane" title="Ethane">Ethane</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Pentane" title="Pentane">Pentane</a></li> <li><a href="/wiki/Hexane" title="Hexane">Hexane</a></li> <li><a href="/wiki/Heptane" title="Heptane">Heptane</a></li> <li><a href="/wiki/Octane" title="Octane">Octane</a></li> <li><a href="/wiki/Nonane" title="Nonane">Nonane</a></li> <li><a href="/wiki/Decane" title="Decane">Decane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutane" title="Isobutane">Isobutane</a></li> <li><a href="/wiki/Isopentane" title="Isopentane">Isopentane</a></li> <li><a href="/wiki/3-Methylpentane" title="3-Methylpentane">3-Methylpentane</a></li> <li><a href="/wiki/Neopentane" title="Neopentane">Neopentane</a></li> <li><a href="/wiki/2-Methylpentane" title="2-Methylpentane">Isohexane</a></li> <li><a href="/wiki/2-Methylhexane" title="2-Methylhexane">Isoheptane</a></li> <li><a href="/wiki/2,2,4-Trimethylpentane" title="2,2,4-Trimethylpentane">Isooctane</a></li> <li><a href="/wiki/2-Methyloctane" title="2-Methyloctane">Isononane</a></li> <li><a href="/w/index.php?title=Isodecane&action=edit&redlink=1" class="new" title="Isodecane (page does not exist)">Isodecane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a></li> <li><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a></li> <li><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></li> <li><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a></li> <li><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a></li> <li><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a></li> <li><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkane&action=edit&redlink=1" class="new" title="Alkylcycloalkane (page does not exist)">Alkylcycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylcyclopropane" title="Methylcyclopropane">Methylcyclopropane</a></li> <li><a href="/w/index.php?title=Methylcyclobutane&action=edit&redlink=1" class="new" title="Methylcyclobutane (page does not exist)">Methylcyclobutane</a></li> <li><a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">Methylcyclopentane</a></li> <li><a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">Methylcyclohexane</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexane&action=edit&redlink=1" class="new" title="Isopropylcyclohexane (page does not exist)">Isopropylcyclohexane</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkane&action=edit&redlink=1" class="new" title="Bicycloalkane (page does not exist)">Bicycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Housane" title="Housane">Housane</a> (bicyclo[2.1.0]pentane)</li> <li><a href="/wiki/Norbornane" title="Norbornane">Norbornane</a> (bicyclo[2.2.1]heptane)</li> <li><a href="/wiki/Decalin" title="Decalin">Decalin</a> (bicyclo[4.4.0]decane)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Polycycloalkane&action=edit&redlink=1" class="new" title="Polycycloalkane (page does not exist)">Polycycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adamantane" title="Adamantane">Adamantane</a></li> <li><a href="/wiki/Diamondoid" title="Diamondoid">Diamondoid</a></li> <li><a href="/w/index.php?title=Perhydrophenanthrene&action=edit&redlink=1" class="new" title="Perhydrophenanthrene (page does not exist)">Perhydrophenanthrene</a></li> <li><a href="/wiki/Sterane" title="Sterane">Sterane</a></li> <li><a href="/wiki/Cubane" title="Cubane">Cubane</a></li> <li><a href="/wiki/Prismane" title="Prismane">Prismane</a></li> <li><a href="/wiki/Dodecahedrane" title="Dodecahedrane">Dodecahedrane</a></li> <li><a href="/wiki/Basketane" title="Basketane">Basketane</a></li> <li><a href="/wiki/Churchane" title="Churchane">Churchane</a></li> <li><a href="/wiki/Pagodane" title="Pagodane">Pagodane</a></li> <li><a href="/wiki/Twistane" title="Twistane">Twistane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Spiroalkane&action=edit&redlink=1" class="new" title="Spiroalkane (page does not exist)">Spiroalkanes</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Unsaturated_hydrocarbon" class="mw-redirect" title="Unsaturated hydrocarbon">Unsaturated</a><br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkene" title="Alkene">Alkenes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i></sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkenes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylene" title="Ethylene">Ethene</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Butene" title="Butene">Butene</a></li> <li><a href="/wiki/Pentene" title="Pentene">Pentene</a></li> <li><a href="/wiki/Hexene" title="Hexene">Hexene</a></li> <li><a href="/wiki/Heptene" title="Heptene">Heptene</a></li> <li><a href="/wiki/Octene" title="Octene">Octene</a></li> <li><a href="/wiki/Nonene" title="Nonene">Nonene</a></li> <li><a href="/wiki/Decene" title="Decene">Decene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutylene" title="Isobutylene">Isobutene</a></li> <li><a href="/wiki/Isopentene" class="mw-redirect" title="Isopentene">Isopentene</a></li> <li><a href="/w/index.php?title=Isohexene&action=edit&redlink=1" class="new" title="Isohexene (page does not exist)">Isohexene</a></li> <li><a href="/w/index.php?title=Isoheptene&action=edit&redlink=1" class="new" title="Isoheptene (page does not exist)">Isoheptene</a></li> <li><a href="/w/index.php?title=Isooctene&action=edit&redlink=1" class="new" title="Isooctene (page does not exist)">Isooctene</a></li> <li><a href="/w/index.php?title=Isononene&action=edit&redlink=1" class="new" title="Isononene (page does not exist)">Isononene</a></li> <li><a href="/w/index.php?title=Isodecene&action=edit&redlink=1" class="new" title="Isodecene (page does not exist)">Isodecene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkyne" title="Alkyne">Alkynes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> − 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkynes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Ethyne</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Butyne" title="Butyne">Butyne</a></li> <li><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a></li> <li><a href="/wiki/3-Hexyne" title="3-Hexyne">Hexyne</a></li> <li><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a></li> <li><a href="/wiki/Octyne" title="Octyne">Octyne</a></li> <li><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a></li> <li><a href="/wiki/1-Decyne" title="1-Decyne">Decyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkynes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Isopentyne&action=edit&redlink=1" class="new" title="Isopentyne (page does not exist)">Isopentyne</a></li> <li><a href="/w/index.php?title=Isohexyne&action=edit&redlink=1" class="new" title="Isohexyne (page does not exist)">Isohexyne</a></li> <li><a href="/w/index.php?title=Isoheptyne&action=edit&redlink=1" class="new" title="Isoheptyne (page does not exist)">Isoheptyne</a></li> <li><a href="/w/index.php?title=Isooctyne&action=edit&redlink=1" class="new" title="Isooctyne (page does not exist)">Isooctyne</a></li> <li><a href="/w/index.php?title=Isononyne&action=edit&redlink=1" class="new" title="Isononyne (page does not exist)">Isononyne</a></li> <li><a href="/w/index.php?title=Isodecyne&action=edit&redlink=1" class="new" title="Isodecyne (page does not exist)">Isodecyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></li> <li><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></li> <li><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></li> <li><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></li> <li><a href="/wiki/Cyclooctene" title="Cyclooctene">Cyclooctene</a></li> <li><a href="/wiki/Cyclononene" title="Cyclononene">Cyclononene</a></li> <li><a href="/wiki/Cyclodecene" title="Cyclodecene">Cyclodecene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkene&action=edit&redlink=1" class="new" title="Alkylcycloalkene (page does not exist)">Alkylcycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Methylcyclopropene" title="1-Methylcyclopropene">Methylcyclopropene</a></li> <li><a href="/w/index.php?title=Methylcyclobutene&action=edit&redlink=1" class="new" title="Methylcyclobutene (page does not exist)">Methylcyclobutene</a></li> <li><a href="/w/index.php?title=Methylcyclopentene&action=edit&redlink=1" class="new" title="Methylcyclopentene (page does not exist)">Methylcyclopentene</a></li> <li><a href="/wiki/Methylcyclohexene" title="Methylcyclohexene">Methylcyclohexene</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexene&action=edit&redlink=1" class="new" title="Isopropylcyclohexene (page does not exist)">Isopropylcyclohexene</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkene&action=edit&redlink=1" class="new" title="Bicycloalkene (page does not exist)">Bicycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Norbornene" title="Norbornene">Norbornene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropyne" class="mw-redirect" title="Cyclopropyne">Cyclopropyne</a></li> <li><a href="/wiki/Cyclobutyne" title="Cyclobutyne">Cyclobutyne</a></li> <li><a href="/wiki/Cyclopentyne" title="Cyclopentyne">Cyclopentyne</a></li> <li><a href="/w/index.php?title=Cyclohexyne&action=edit&redlink=1" class="new" title="Cyclohexyne (page does not exist)">Cyclohexyne</a></li> <li><a href="/w/index.php?title=Cycloheptyne&action=edit&redlink=1" class="new" title="Cycloheptyne (page does not exist)">Cycloheptyne</a></li> <li><a href="/wiki/Cyclooctyne" title="Cyclooctyne">Cyclooctyne</a></li> <li><a href="/w/index.php?title=Cyclononyne&action=edit&redlink=1" class="new" title="Cyclononyne (page does not exist)">Cyclononyne</a></li> <li><a href="/w/index.php?title=Cyclodecyne&action=edit&redlink=1" class="new" title="Cyclodecyne (page does not exist)">Cyclodecyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Diene" title="Diene">Dienes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propadiene" title="Propadiene">Propadiene</a></li> <li><a href="/wiki/Butadiene" title="Butadiene">Butadiene</a></li> <li><a href="/wiki/Piperylene" title="Piperylene">Pentadiene</a></li> <li><a href="/wiki/1,5-Hexadiene" title="1,5-Hexadiene">Hexadiene</a></li> <li><a href="/w/index.php?title=Heptadiene&action=edit&redlink=1" class="new" title="Heptadiene (page does not exist)">Heptadiene</a></li> <li><a href="/wiki/1,7-Octadiene" title="1,7-Octadiene">Octadiene</a></li> <li><a href="/w/index.php?title=Nonadiene&action=edit&redlink=1" class="new" title="Nonadiene (page does not exist)">Nonadiene</a></li> <li><a href="/w/index.php?title=Decadiene&action=edit&redlink=1" class="new" title="Decadiene (page does not exist)">Decadiene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Alkatriene&action=edit&redlink=1" class="new" title="Alkatriene (page does not exist)">Alkatriene</a></li> <li><a href="/w/index.php?title=Alkadiyne&action=edit&redlink=1" class="new" title="Alkadiyne (page does not exist)">Alkadiyne</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li> <li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclododecatriene" title="Cyclododecatriene">Cyclododecatriene</a></li> <li><a href="/wiki/Enyne" title="Enyne">Enyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic<br />hydrocarbons</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">PAHs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Acene" title="Acene">Acenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicenes</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulenes</a></li> <li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a class="mw-selflink selflink">Phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">Alkylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C2-Benzenes" title="C2-Benzenes">C2-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Xylene" title="Xylene">Xylenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Xylene" title="O-Xylene"><i>o</i>-Xylene</a></li> <li><a href="/wiki/M-Xylene" title="M-Xylene"><i>m</i>-Xylene</a></li> <li><a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-Xylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylbenzene" title="Ethylbenzene">Ethylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C3-Benzenes" title="C3-Benzenes">C3-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Trimethylbenzenes" class="mw-redirect" title="Trimethylbenzenes">Trimethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mesitylene" title="Mesitylene">Mesitylene</a></li> <li><a href="/wiki/Pseudocumene" class="mw-redirect" title="Pseudocumene">Pseudocumene</a></li> <li><a href="/wiki/Hemellitene" class="mw-redirect" title="Hemellitene">Hemellitene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cumene" title="Cumene">Cumene</a></li> <li><a href="/wiki/N-Propylbenzene" title="N-Propylbenzene"><i>n</i>-Propylbenzene</a></li> <li><a href="/wiki/4-Ethyltoluene" title="4-Ethyltoluene">4-Ethyltoluene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C4-Benzenes" title="C4-Benzenes">C4-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cymenes" class="mw-redirect" title="Cymenes">Cymenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Cymene" title="O-Cymene"><i>o</i>-Cymene</a></li> <li><a href="/wiki/M-Cymene" title="M-Cymene"><i>m</i>-Cymene</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene"><i>p</i>-Cymene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Tetramethylbenzenes" class="mw-redirect" title="Tetramethylbenzenes">Tetramethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Durene" title="Durene">Durene</a></li> <li><a href="/wiki/Prehnitene" title="Prehnitene">Prehnitene</a></li> <li><a href="/wiki/Isodurene" title="Isodurene">Isodurene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N-Butylbenzene" title="N-Butylbenzene"><i>n</i>-Butylbenzene</a></li> <li><a href="/wiki/Sec-Butylbenzene" title="Sec-Butylbenzene"><i>sec</i>-Butylbenzene</a></li> <li><a href="/wiki/Tert-Butylbenzene" title="Tert-Butylbenzene"><i>tert</i>-Butylbenzene</a></li> <li><a href="/wiki/Isobutylbenzene" title="Isobutylbenzene">Isobutylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hexamethylbenzene" title="Hexamethylbenzene">Hexamethylbenzene</a></li> <li><a href="/wiki/2-Phenylhexane" title="2-Phenylhexane">2-Phenylhexane</a></li> <li><a href="/wiki/1,3,5-Triethylbenzene" title="1,3,5-Triethylbenzene">1,3,5-Triethylbenzene</a></li> <li><a href="/wiki/1,3,5-Triheptylbenzene" title="1,3,5-Triheptylbenzene">1,3,5-Triheptylbenzene</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Vinylbenzenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Styrene" title="Styrene">Styrene</a></li> <li><a href="/wiki/Divinylbenzene" title="Divinylbenzene">Divinylbenzene</a></li> <li><a href="/wiki/4-Vinyltoluene" title="4-Vinyltoluene">4-Vinyltoluene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Phenylacetylene" title="Phenylacetylene">Phenylacetylene</a></li> <li><a href="/wiki/Trans-Propenylbenzene" title="Trans-Propenylbenzene"><i>trans</i>-Propenylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Annulene" title="Annulene">Annulenes</a></li> <li><a href="/wiki/Annulyne" title="Annulyne">Annulynes</a></li> <li><a href="/wiki/Alicyclic_compound" title="Alicyclic compound">Alicyclic compounds</a></li> <li><a href="/wiki/Petroleum_jelly" title="Petroleum jelly">Petroleum jelly</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Polycyclic_aromatic_hydrocarbons94" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="text-align: center;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:PAHs" title="Template:PAHs"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:PAHs" title="Template talk:PAHs"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:PAHs" title="Special:EditPage/Template:PAHs"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Polycyclic_aromatic_hydrocarbons94" style="font-size:114%;margin:0 4em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbons</a></div></th></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">2 rings</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">3 rings</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acenaphthene" title="Acenaphthene">Acenaphthene</a></li> <li><a href="/wiki/Acenaphthylene" title="Acenaphthylene">Acenaphthylene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Phenalene" title="Phenalene">Phenalene</a></li> <li><a class="mw-selflink selflink">Phenanthrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">4 rings</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benz(a)anthracene" title="Benz(a)anthracene">Benz[<i>a</i>]anthracene</a></li> <li><a href="/wiki/Benzo(a)fluorene" title="Benzo(a)fluorene">Benzo[<i>a</i>]fluorene</a></li> <li><a href="/wiki/Benzo(c)fluorene" title="Benzo(c)fluorene">Benzo[<i>c</i>]fluorene</a></li> <li><a href="/wiki/Benzo(c)phenanthrene" title="Benzo(c)phenanthrene">Benzo[<i>c</i>]phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Fluoranthene" title="Fluoranthene">Fluoranthene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Triphenylene" title="Triphenylene">Triphenylene</a></li> <li><a href="/wiki/Tricyclobutabenzene" title="Tricyclobutabenzene">Tricyclobutabenzene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">5 rings</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benz(e)acephenanthrylene" title="Benz(e)acephenanthrylene">Benz[<i>e</i>]acephenanthrylene</a></li> <li><a href="/wiki/Benzopyrene" title="Benzopyrene">Benzopyrene</a> <ul><li><a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">Benzo[<i>a</i>]pyrene</a></li> <li><a href="/wiki/Benzo(e)pyrene" title="Benzo(e)pyrene">Benzo[<i>e</i>]pyrene</a></li> <li><a href="/wiki/Olympicene" title="Olympicene">6<i>H</i>-Benzo[<i>cd</i>]pyrene(Olympicene)</a></li></ul></li> <li><a href="/wiki/Benzo(a)fluoranthene" title="Benzo(a)fluoranthene">Benzo[<i>a</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(b)fluoranthene" class="mw-redirect" title="Benzo(b)fluoranthene">Benzo[<i>b</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(j)fluoranthene" title="Benzo(j)fluoranthene">Benzo[<i>j</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(k)fluoranthene" title="Benzo(k)fluoranthene">Benzo[<i>k</i>]fluoranthene</a></li> <li><a href="/wiki/Bicalicene" title="Bicalicene">trans-Bicalicene</a></li> <li><a href="/wiki/Dibenz(a,h)anthracene" title="Dibenz(a,h)anthracene">Dibenz[<i>a</i>,<i>h</i>]anthracene</a></li> <li><a href="/wiki/Dibenz(a,j)anthracene" title="Dibenz(a,j)anthracene">Dibenz[<i>a</i>,<i>j</i>]anthracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/w/index.php?title=Pentaphene&action=edit&redlink=1" class="new" title="Pentaphene (page does not exist)">Pentaphene</a></li> <li><a href="/wiki/Perylene" title="Perylene">Perylene</a></li> <li><a href="/wiki/Picene" title="Picene">Picene</a></li> <li><a href="/wiki/Tetraphenylene" title="Tetraphenylene">Tetraphenylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">6 rings</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthanthrene" title="Anthanthrene">Anthanthrene</a></li> <li><a href="/wiki/Benzo(ghi)perylene" title="Benzo(ghi)perylene">Benzo[<i>ghi</i>]perylene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Dibenzopyrenes" title="Dibenzopyrenes">Dibenzopyrenes</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Triangulene" title="Triangulene">Triangulene</a></li> <li><a href="/wiki/Zethrene" title="Zethrene">Zethrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">7+ rings</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coronene" title="Coronene">Coronene</a></li> <li><a href="/wiki/Dicoronylene" title="Dicoronylene">Dicoronylene</a></li> <li><a href="/wiki/Diindenoperylene" title="Diindenoperylene">Diindenoperylene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li> <li><a href="/wiki/Hexabenzocoronene" title="Hexabenzocoronene">Hexabenzocoronene</a> (<a href="/wiki/Hexa-cata-hexabenzocoronene" title="Hexa-cata-hexabenzocoronene">Hexa-cata-</a>)</li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li> <li><a href="/wiki/Ovalene" title="Ovalene">Ovalene</a></li> <li><a href="/wiki/Rubicene" title="Rubicene">Rubicene</a></li> <li><a href="/wiki/Rubrene" title="Rubrene">Rubrene</a></li> <li><a href="/wiki/Sumanene" title="Sumanene">Sumanene</a></li> <li><a href="/wiki/Superphenalene" title="Superphenalene">Superphenalene</a></li> <li><a href="/wiki/Trinaphthylene" title="Trinaphthylene">Trinaphthylene</a></li> <li><a href="/wiki/Truxene" title="Truxene">Truxene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">General classes</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acene" title="Acene">Acene</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulene</a></li> <li><a href="/wiki/Cyclacene" title="Cyclacene">Cyclacene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicene</a></li> <li><a href="/wiki/Phenacene" title="Phenacene">Phenacene</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Topics_in_organic_reactions48" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Organic_reactions" title="Template:Organic reactions"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Organic_reactions" title="Template talk:Organic reactions"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Organic_reactions" title="Special:EditPage/Template:Organic reactions"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Topics_in_organic_reactions48" style="font-size:114%;margin:0 4em">Topics in <a href="/wiki/Organic_reaction" title="Organic reaction">organic reactions</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Addition_reaction" title="Addition reaction">Addition reaction</a></li> <li><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reaction</a></li> <li><a href="/wiki/Polymerization" title="Polymerization">Polymerization</a></li> <li><a href="/wiki/Category:Reagents_for_organic_chemistry" title="Category:Reagents for organic chemistry">Reagents</a></li> <li><a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">Rearrangement reaction</a></li> <li><a href="/wiki/Organic_redox_reaction" title="Organic redox reaction">Redox reaction</a></li> <li><a href="/wiki/Regioselectivity" title="Regioselectivity">Regioselectivity</a></li> <li><a href="/wiki/Stereoselectivity" title="Stereoselectivity">Stereoselectivity</a></li> <li><a href="/wiki/Stereospecificity" title="Stereospecificity">Stereospecificity</a></li> <li><a href="/wiki/Substitution_reaction" title="Substitution reaction">Substitution reaction</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/A_value" title="A value">A value</a></li> <li><a href="/wiki/Alpha_effect" title="Alpha effect">Alpha effect</a></li> <li><a href="/wiki/Annulene" title="Annulene">Annulene</a></li> <li><a href="/wiki/Anomeric_effect" title="Anomeric effect">Anomeric effect</a></li> <li><a href="/wiki/Antiaromaticity" title="Antiaromaticity">Antiaromaticity</a></li> <li><a href="/wiki/Aromatic_ring_current" title="Aromatic ring current">Aromatic ring current</a></li> <li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a></li> <li><a href="/wiki/Baird%27s_rule" title="Baird's rule">Baird's rule</a></li> <li><a href="/wiki/Baker%E2%80%93Nathan_effect" title="Baker–Nathan effect">Baker–Nathan effect</a></li> <li><a href="/wiki/Baldwin%27s_rules" title="Baldwin's rules">Baldwin's rules</a></li> <li><a href="/wiki/Bema_Hapothle" title="Bema Hapothle">Bema Hapothle</a></li> <li><a href="/wiki/Beta-silicon_effect" class="mw-redirect" title="Beta-silicon effect">Beta-silicon effect</a></li> <li><a href="/wiki/Bicycloaromaticity" title="Bicycloaromaticity">Bicycloaromaticity</a></li> <li><a href="/wiki/Bredt%27s_rule" title="Bredt's rule">Bredt's rule</a></li> <li><a href="/wiki/B%C3%BCrgi%E2%80%93Dunitz_angle" title="Bürgi–Dunitz angle">Bürgi–Dunitz angle</a></li> <li><a href="/wiki/Catalytic_resonance_theory" title="Catalytic resonance theory">Catalytic resonance theory</a></li> <li><a href="/wiki/Charge_remote_fragmentation" class="mw-redirect" title="Charge remote fragmentation">Charge remote fragmentation</a></li> <li><a href="/wiki/Charge-transfer_complex" title="Charge-transfer complex">Charge-transfer complex</a></li> <li><a href="/wiki/Clar%27s_rule" title="Clar's rule">Clar's rule</a></li> <li><a href="/wiki/Conformational_isomerism" class="mw-redirect" title="Conformational isomerism">Conformational isomerism</a></li> <li><a href="/wiki/Conjugated_system" title="Conjugated system">Conjugated system</a></li> <li><a href="/wiki/Conrotatory_and_disrotatory" title="Conrotatory and disrotatory">Conrotatory and disrotatory</a></li> <li><a href="/wiki/Curtin%E2%80%93Hammett_principle" title="Curtin–Hammett principle">Curtin–Hammett principle</a></li> <li><a href="/wiki/Dynamic_binding_(chemistry)" title="Dynamic binding (chemistry)">Dynamic binding (chemistry)</a></li> <li><a href="/wiki/Edwards_equation" title="Edwards equation">Edwards equation</a></li> <li><a href="/wiki/Effective_molarity" title="Effective molarity">Effective molarity</a></li> <li><a href="/wiki/Electromeric_effect" title="Electromeric effect">Electromeric effect</a></li> <li><a href="/wiki/Electron-rich" title="Electron-rich">Electron-rich</a></li> <li><a href="/wiki/Electron-withdrawing_group" title="Electron-withdrawing group">Electron-withdrawing group</a></li> <li><a href="/wiki/Electronic_effect" title="Electronic effect">Electronic effect</a></li> <li><a href="/wiki/Electrophile" title="Electrophile">Electrophile</a></li> <li><a href="/wiki/Evelyn_effect" title="Evelyn effect">Evelyn effect</a></li> <li><a href="/wiki/Flippin%E2%80%93Lodge_angle" title="Flippin–Lodge angle">Flippin–Lodge angle</a></li> <li><a href="/wiki/Free-energy_relationship" title="Free-energy relationship">Free-energy relationship</a></li> <li><a href="/wiki/Grunwald%E2%80%93Winstein_equation" title="Grunwald–Winstein equation">Grunwald–Winstein equation</a></li> <li><a href="/wiki/Hammett_acidity_function" title="Hammett acidity function">Hammett acidity function</a></li> <li><a href="/wiki/Hammett_equation" title="Hammett equation">Hammett equation</a></li> <li><a href="/wiki/George_S._Hammond" title="George S. Hammond">George S. Hammond</a></li> <li><a href="/wiki/Hammond%27s_postulate" title="Hammond's postulate">Hammond's postulate</a></li> <li><a href="/wiki/Homoaromaticity" title="Homoaromaticity">Homoaromaticity</a></li> <li><a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a></li> <li><a href="/wiki/Hyperconjugation" title="Hyperconjugation">Hyperconjugation</a></li> <li><a href="/wiki/Inductive_effect" title="Inductive effect">Inductive effect</a></li> <li><a href="/wiki/Kinetic_isotope_effect" title="Kinetic isotope effect">Kinetic isotope effect</a></li> <li><a href="/wiki/LFER_solvent_coefficients_(data_page)" title="LFER solvent coefficients (data page)">LFER solvent coefficients (data page)</a></li> <li><a href="/wiki/Marcus_theory" title="Marcus theory">Marcus theory</a></li> <li><a href="/wiki/Markovnikov%27s_rule" title="Markovnikov's rule">Markovnikov's rule</a></li> <li><a href="/wiki/M%C3%B6bius_aromaticity" title="Möbius aromaticity">Möbius aromaticity</a></li> <li><a href="/wiki/M%C3%B6bius%E2%80%93H%C3%BCckel_concept" title="Möbius–Hückel concept">Möbius–Hückel concept</a></li> <li><a href="/wiki/More_O%27Ferrall%E2%80%93Jencks_plot" title="More O'Ferrall–Jencks plot">More O'Ferrall–Jencks plot</a></li> <li><a href="/wiki/Negative_hyperconjugation" title="Negative hyperconjugation">Negative hyperconjugation</a></li> <li><a href="/wiki/Neighbouring_group_participation" title="Neighbouring group participation">Neighbouring group participation</a></li> <li><a href="/wiki/2-Norbornyl_cation" title="2-Norbornyl cation">2-Norbornyl cation</a></li> <li><a href="/wiki/Nucleophile" title="Nucleophile">Nucleophile</a></li> <li><a href="/wiki/Kennedy_J._P._Orton" title="Kennedy J. P. Orton">Kennedy J. P. Orton</a></li> <li><a href="/wiki/Passive_binding" title="Passive binding">Passive binding</a></li> <li><a href="/wiki/Phosphaethynolate" title="Phosphaethynolate">Phosphaethynolate</a></li> <li><a href="/wiki/Polar_effect" class="mw-redirect" title="Polar effect">Polar effect</a></li> <li><a href="/wiki/Polyfluorene" title="Polyfluorene">Polyfluorene</a></li> <li><a href="/wiki/Ring_strain" title="Ring strain">Ring strain</a></li> <li><a href="/wiki/%CE%A3-aromaticity" class="mw-redirect" title="Σ-aromaticity">Σ-aromaticity</a></li> <li><a href="/wiki/Spherical_aromaticity" title="Spherical aromaticity">Spherical aromaticity</a></li> <li><a href="/wiki/Spiroaromaticity" class="mw-redirect" title="Spiroaromaticity">Spiroaromaticity</a></li> <li><a href="/wiki/Steric_effects" title="Steric effects">Steric effects</a></li> <li><a href="/wiki/Superaromaticity" class="mw-redirect" title="Superaromaticity">Superaromaticity</a></li> <li><a href="/wiki/Swain%E2%80%93Lupton_equation" title="Swain–Lupton equation">Swain–Lupton equation</a></li> <li><a href="/wiki/Taft_equation" title="Taft equation">Taft equation</a></li> <li><a href="/wiki/Thorpe%E2%80%93Ingold_effect" title="Thorpe–Ingold effect">Thorpe–Ingold effect</a></li> <li><a href="/wiki/Vinylogy" title="Vinylogy">Vinylogy</a></li> <li><a href="/wiki/Walsh_diagram" title="Walsh diagram">Walsh diagram</a></li> <li><a href="/wiki/Woodward%E2%80%93Hoffmann_rules" title="Woodward–Hoffmann rules">Woodward–Hoffmann rules</a></li> <li><a href="/wiki/Woodward%27s_rules" title="Woodward's rules">Woodward's rules</a></li> <li><a href="/wiki/Y-aromaticity" class="mw-redirect" title="Y-aromaticity">Y-aromaticity</a></li> <li><a href="/wiki/Yukawa%E2%80%93Tsuno_equation" title="Yukawa–Tsuno equation">Yukawa–Tsuno equation</a></li> <li><a href="/wiki/Zaitsev%27s_rule" class="mw-redirect" title="Zaitsev's rule">Zaitsev's rule</a></li> <li><a href="/wiki/%CE%A3-bishomoaromaticity" class="mw-redirect" title="Σ-bishomoaromaticity">Σ-bishomoaromaticity</a></li></ul> </div><table class="nowraplinks mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="List_of_organic_reactions315" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_organic_reactions" title="List of organic reactions">List of organic reactions</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:7.5em">Carbon-carbon <br /> bond forming <br /> reactions</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetoacetic_ester_synthesis" title="Acetoacetic ester synthesis">Acetoacetic ester synthesis</a></li> <li><a href="/wiki/Acyloin_condensation" title="Acyloin condensation">Acyloin condensation</a></li> <li><a href="/wiki/Aldol_condensation" title="Aldol condensation">Aldol condensation</a></li> <li><a href="/wiki/Aldol_reaction" title="Aldol reaction">Aldol reaction</a></li> <li><a href="/wiki/Alkane_metathesis" title="Alkane metathesis">Alkane metathesis</a></li> <li><a href="/wiki/Alkyne_metathesis" title="Alkyne metathesis">Alkyne metathesis</a></li> <li><a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Alkyne trimerisation</a></li> <li><a href="/wiki/Alkynylation" title="Alkynylation">Alkynylation</a></li> <li><a href="/wiki/Allan%E2%80%93Robinson_reaction" title="Allan–Robinson reaction">Allan–Robinson reaction</a></li> <li><a href="/wiki/Arndt%E2%80%93Eistert_reaction" title="Arndt–Eistert reaction">Arndt–Eistert reaction</a></li> <li><a href="/wiki/Auwers_synthesis" title="Auwers synthesis">Auwers synthesis</a></li> <li><a href="/wiki/Aza-Baylis%E2%80%93Hillman_reaction" title="Aza-Baylis–Hillman reaction">Aza-Baylis–Hillman reaction</a></li> <li><a href="/wiki/Barbier_reaction" title="Barbier reaction">Barbier reaction</a></li> <li><a href="/wiki/Barton%E2%80%93Kellogg_reaction" title="Barton–Kellogg reaction">Barton–Kellogg reaction</a></li> <li><a href="/wiki/Baylis%E2%80%93Hillman_reaction" title="Baylis–Hillman reaction">Baylis–Hillman reaction</a></li> <li><a href="/wiki/Benary_reaction" title="Benary reaction">Benary reaction</a></li> <li><a href="/wiki/Bergman_cyclization" title="Bergman cyclization">Bergman cyclization</a></li> <li><a href="/wiki/Biginelli_reaction" title="Biginelli reaction">Biginelli reaction</a></li> <li><a href="/wiki/Bingel_reaction" title="Bingel reaction">Bingel reaction</a></li> <li><a href="/wiki/Blaise_ketone_synthesis" title="Blaise ketone synthesis">Blaise ketone synthesis</a></li> <li><a href="/wiki/Blaise_reaction" title="Blaise reaction">Blaise reaction</a></li> <li><a href="/wiki/Blanc_chloromethylation" title="Blanc chloromethylation">Blanc chloromethylation</a></li> <li><a href="/wiki/Bodroux%E2%80%93Chichibabin_aldehyde_synthesis" title="Bodroux–Chichibabin aldehyde synthesis">Bodroux–Chichibabin aldehyde synthesis</a></li> <li><a href="/wiki/Bouveault_aldehyde_synthesis" title="Bouveault aldehyde synthesis">Bouveault aldehyde synthesis</a></li> <li><a href="/wiki/Bucherer%E2%80%93Bergs_reaction" title="Bucherer–Bergs reaction">Bucherer–Bergs reaction</a></li> <li><a href="/wiki/Buchner_ring_expansion" title="Buchner ring expansion">Buchner ring expansion</a></li> <li><a href="/wiki/Cadiot%E2%80%93Chodkiewicz_coupling" title="Cadiot–Chodkiewicz coupling">Cadiot–Chodkiewicz coupling</a></li> <li><a href="/wiki/Carbonyl_allylation" title="Carbonyl allylation">Carbonyl allylation</a></li> <li><a href="/wiki/Carbonyl_olefin_metathesis" title="Carbonyl olefin metathesis">Carbonyl olefin metathesis</a></li> <li><a href="/wiki/Castro%E2%80%93Stephens_coupling" title="Castro–Stephens coupling">Castro–Stephens coupling</a></li> <li><a href="/wiki/Chan_rearrangement" title="Chan rearrangement">Chan rearrangement</a></li> <li><a href="/wiki/Chan%E2%80%93Lam_coupling" title="Chan–Lam coupling">Chan–Lam coupling</a></li> <li><a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen condensation</a></li> <li><a href="/wiki/Claisen_rearrangement" title="Claisen rearrangement">Claisen rearrangement</a></li> <li><a href="/wiki/Claisen-Schmidt_condensation" class="mw-redirect" title="Claisen-Schmidt condensation">Claisen-Schmidt condensation</a></li> <li><a href="/wiki/Combes_quinoline_synthesis" title="Combes quinoline synthesis">Combes quinoline synthesis</a></li> <li><a href="/wiki/Corey%E2%80%93Fuchs_reaction" title="Corey–Fuchs reaction">Corey–Fuchs reaction</a></li> <li><a href="/wiki/Corey%E2%80%93House_synthesis" title="Corey–House synthesis">Corey–House synthesis</a></li> <li><a href="/wiki/Coupling_reaction" title="Coupling reaction">Coupling reaction</a></li> <li><a href="/wiki/Cross-coupling_reaction" title="Cross-coupling reaction">Cross-coupling reaction</a></li> <li><a href="/wiki/Cross_dehydrogenative_coupling" title="Cross dehydrogenative coupling">Cross dehydrogenative coupling</a></li> <li><a href="/wiki/Cross-coupling_partner" title="Cross-coupling partner">Cross-coupling partner</a></li> <li><a href="/wiki/Dakin%E2%80%93West_reaction" title="Dakin–West reaction">Dakin–West reaction</a></li> <li><a href="/wiki/Darzens_reaction" title="Darzens reaction">Darzens reaction</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Doebner_reaction" title="Doebner reaction">Doebner reaction</a></li> <li><a href="/wiki/Wulff%E2%80%93D%C3%B6tz_reaction" title="Wulff–Dötz reaction">Wulff–Dötz reaction</a></li> <li><a href="/wiki/Ene_reaction" title="Ene reaction">Ene reaction</a></li> <li><a href="/wiki/Enyne_metathesis" title="Enyne metathesis">Enyne metathesis</a></li> <li><a href="/wiki/Ethenolysis" title="Ethenolysis">Ethenolysis</a></li> <li><a href="/wiki/Favorskii_reaction" title="Favorskii reaction">Favorskii reaction</a></li> <li><a href="/wiki/Ferrier_carbocyclization" title="Ferrier carbocyclization">Ferrier carbocyclization</a></li> <li><a href="/wiki/Friedel%E2%80%93Crafts_reaction" title="Friedel–Crafts reaction">Friedel–Crafts reaction</a></li> <li><a href="/wiki/Fujimoto%E2%80%93Belleau_reaction" title="Fujimoto–Belleau reaction">Fujimoto–Belleau reaction</a></li> <li><a href="/wiki/Fujiwara%E2%80%93Moritani_reaction" title="Fujiwara–Moritani reaction">Fujiwara–Moritani reaction</a></li> <li><a href="/wiki/Fukuyama_coupling" title="Fukuyama coupling">Fukuyama coupling</a></li> <li><a href="/wiki/Gabriel%E2%80%93Colman_rearrangement" title="Gabriel–Colman rearrangement">Gabriel–Colman rearrangement</a></li> <li><a href="/wiki/Gattermann_reaction" title="Gattermann reaction">Gattermann reaction</a></li> <li><a href="/wiki/Glaser_coupling" title="Glaser coupling">Glaser coupling</a></li> <li><a href="/wiki/Grignard_reaction" title="Grignard reaction">Grignard reaction</a></li> <li><a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagent</a></li> <li><a href="/wiki/Hammick_reaction" title="Hammick reaction">Hammick reaction</a></li> <li><a href="/wiki/Heck_reaction" title="Heck reaction">Heck reaction</a></li> <li><a href="/wiki/Henry_reaction" title="Henry reaction">Henry reaction</a></li> <li><a href="/wiki/Heterogeneous_metal_catalyzed_cross-coupling" title="Heterogeneous metal catalyzed cross-coupling">Heterogeneous metal catalyzed cross-coupling</a></li> <li><a href="/wiki/High_dilution_principle" title="High dilution principle">High dilution principle</a></li> <li><a href="/wiki/Hiyama_coupling" title="Hiyama coupling">Hiyama coupling</a></li> <li><a href="/wiki/Homologation_reaction" title="Homologation reaction">Homologation reaction</a></li> <li><a href="/wiki/Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction" title="Horner–Wadsworth–Emmons reaction">Horner–Wadsworth–Emmons reaction</a></li> <li><a href="/wiki/Hydrocyanation" title="Hydrocyanation">Hydrocyanation</a></li> <li><a href="/wiki/Hydrovinylation" title="Hydrovinylation">Hydrovinylation</a></li> <li><a href="/wiki/Hydroxymethylation" title="Hydroxymethylation">Hydroxymethylation</a></li> <li><a href="/wiki/Ivanov_reaction" title="Ivanov reaction">Ivanov reaction</a></li> <li><a href="/wiki/Johnson%E2%80%93Corey%E2%80%93Chaykovsky_reaction" title="Johnson–Corey–Chaykovsky reaction">Johnson–Corey–Chaykovsky reaction</a></li> <li><a href="/wiki/Julia_olefination" title="Julia olefination">Julia olefination</a></li> <li><a href="/wiki/Julia%E2%80%93Kocienski_olefination" class="mw-redirect" title="Julia–Kocienski olefination">Julia–Kocienski olefination</a></li> <li><a href="/wiki/Kauffmann_olefination" title="Kauffmann olefination">Kauffmann olefination</a></li> <li><a href="/wiki/Knoevenagel_condensation" title="Knoevenagel condensation">Knoevenagel condensation</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Kolbe%E2%80%93Schmitt_reaction" title="Kolbe–Schmitt reaction">Kolbe–Schmitt reaction</a></li> <li><a href="/wiki/Kowalski_ester_homologation" title="Kowalski ester homologation">Kowalski ester homologation</a></li> <li><a href="/wiki/Kulinkovich_reaction" title="Kulinkovich reaction">Kulinkovich reaction</a></li> <li><a href="/wiki/Kumada_coupling" title="Kumada coupling">Kumada coupling</a></li> <li><a href="/wiki/Liebeskind%E2%80%93Srogl_coupling" title="Liebeskind–Srogl coupling">Liebeskind–Srogl coupling</a></li> <li><a href="/wiki/Malonic_ester_synthesis" title="Malonic ester synthesis">Malonic ester synthesis</a></li> <li><a href="/wiki/Mannich_reaction" title="Mannich reaction">Mannich reaction</a></li> <li><a href="/wiki/McMurry_reaction" title="McMurry reaction">McMurry reaction</a></li> <li><a href="/wiki/Meerwein_arylation" title="Meerwein arylation">Meerwein arylation</a></li> <li><a href="/wiki/Methylenation" title="Methylenation">Methylenation</a></li> <li><a href="/wiki/Michael_reaction" class="mw-redirect" title="Michael reaction">Michael reaction</a></li> <li><a href="/wiki/Minisci_reaction" title="Minisci reaction">Minisci reaction</a></li> <li><a href="/w/index.php?title=Mizoroki-Heck_vs._Reductive_Heck&action=edit&redlink=1" class="new" title="Mizoroki-Heck vs. Reductive Heck (page does not exist)">Mizoroki-Heck vs. Reductive Heck</a></li> <li><a href="/wiki/Nef_isocyanide_reaction" title="Nef isocyanide reaction">Nef isocyanide reaction</a></li> <li><a href="/wiki/Nef_synthesis" title="Nef synthesis">Nef synthesis</a></li> <li><a href="/wiki/Negishi_coupling" title="Negishi coupling">Negishi coupling</a></li> <li><a href="/wiki/Nierenstein_reaction" title="Nierenstein reaction">Nierenstein reaction</a></li> <li><a href="/wiki/Nitro-Mannich_reaction" title="Nitro-Mannich reaction">Nitro-Mannich reaction</a></li> <li><a href="/wiki/Nozaki%E2%80%93Hiyama%E2%80%93Kishi_reaction" title="Nozaki–Hiyama–Kishi reaction">Nozaki–Hiyama–Kishi reaction</a></li> <li><a href="/wiki/Olefin_conversion_technology" title="Olefin conversion technology">Olefin conversion technology</a></li> <li><a href="/wiki/Olefin_metathesis" title="Olefin metathesis">Olefin metathesis</a></li> <li><a href="/wiki/Palladium%E2%80%93NHC_complex" title="Palladium–NHC complex">Palladium–NHC complex</a></li> <li><a href="/wiki/Passerini_reaction" title="Passerini reaction">Passerini reaction</a></li> <li><a href="/wiki/Peterson_olefination" title="Peterson olefination">Peterson olefination</a></li> <li><a href="/wiki/Pfitzinger_reaction" title="Pfitzinger reaction">Pfitzinger reaction</a></li> <li><a href="/wiki/Piancatelli_rearrangement" title="Piancatelli rearrangement">Piancatelli rearrangement</a></li> <li><a href="/wiki/Pinacol_coupling_reaction" title="Pinacol coupling reaction">Pinacol coupling reaction</a></li> <li><a href="/wiki/Prins_reaction" title="Prins reaction">Prins reaction</a></li> <li><a href="/wiki/Quelet_reaction" title="Quelet reaction">Quelet reaction</a></li> <li><a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a></li> <li><a href="/wiki/Rauhut%E2%80%93Currier_reaction" title="Rauhut–Currier reaction">Rauhut–Currier reaction</a></li> <li><a href="/wiki/Reformatsky_reaction" title="Reformatsky reaction">Reformatsky reaction</a></li> <li><a href="/wiki/Reimer%E2%80%93Tiemann_reaction" title="Reimer–Tiemann reaction">Reimer–Tiemann reaction</a></li> <li><a href="/wiki/Rieche_formylation" title="Rieche formylation">Rieche formylation</a></li> <li><a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">Ring-closing metathesis</a></li> <li><a href="/wiki/Robinson_annulation" title="Robinson annulation">Robinson annulation</a></li> <li><a href="/wiki/Sakurai_reaction" title="Sakurai reaction">Sakurai reaction</a></li> <li><a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a></li> <li><a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a></li> <li><a href="/wiki/Sonogashira_coupling" title="Sonogashira coupling">Sonogashira coupling</a></li> <li><a href="/wiki/Stetter_reaction" title="Stetter reaction">Stetter reaction</a></li> <li><a href="/wiki/Stille_reaction" title="Stille reaction">Stille reaction</a></li> <li><a href="/wiki/Stoll%C3%A9_synthesis" title="Stollé synthesis">Stollé synthesis</a></li> <li><a href="/wiki/Stork_enamine_alkylation" title="Stork enamine alkylation">Stork enamine alkylation</a></li> <li><a href="/wiki/Suzuki_reaction" title="Suzuki reaction">Suzuki reaction</a></li> <li><a href="/wiki/Takai_olefination" title="Takai olefination">Takai olefination</a></li> <li><a href="/wiki/Thermal_rearrangement_of_aromatic_hydrocarbons" title="Thermal rearrangement of aromatic hydrocarbons">Thermal rearrangement of aromatic hydrocarbons</a></li> <li><a href="/wiki/Thorpe_reaction" title="Thorpe reaction">Thorpe reaction</a></li> <li><a href="/wiki/Ugi_reaction" title="Ugi reaction">Ugi reaction</a></li> <li><a href="/wiki/Ullmann_reaction" title="Ullmann reaction">Ullmann reaction</a></li> <li><a href="/wiki/Wagner-Jauregg_reaction" title="Wagner-Jauregg reaction">Wagner-Jauregg reaction</a></li> <li><a href="/wiki/Weinreb_ketone_synthesis" title="Weinreb ketone synthesis">Weinreb ketone synthesis</a></li> <li><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li> <li><a href="/wiki/Wurtz_reaction" title="Wurtz reaction">Wurtz reaction</a></li> <li><a href="/wiki/Wurtz%E2%80%93Fittig_reaction" title="Wurtz–Fittig reaction">Wurtz–Fittig reaction</a></li> <li><a href="/wiki/Zincke%E2%80%93Suhl_reaction" title="Zincke–Suhl reaction">Zincke–Suhl reaction</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Homologation_reactions" class="mw-redirect" title="Homologation reactions">Homologation reactions</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arndt%E2%80%93Eistert_reaction" title="Arndt–Eistert reaction">Arndt–Eistert reaction</a></li> <li><a href="/wiki/Hooker_reaction" title="Hooker reaction">Hooker reaction</a></li> <li><a href="/wiki/Kiliani%E2%80%93Fischer_synthesis" title="Kiliani–Fischer synthesis">Kiliani–Fischer synthesis</a></li> <li><a href="/wiki/Kowalski_ester_homologation" title="Kowalski ester homologation">Kowalski ester homologation</a></li> <li><a href="/wiki/Methoxymethylenetriphenylphosphorane" title="Methoxymethylenetriphenylphosphorane">Methoxymethylenetriphenylphosphorane</a></li> <li><a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a></li> <li><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Olefination reactions</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bamford%E2%80%93Stevens_reaction" title="Bamford–Stevens reaction">Bamford–Stevens reaction</a></li> <li><a href="/wiki/Barton%E2%80%93Kellogg_reaction" title="Barton–Kellogg reaction">Barton–Kellogg reaction</a></li> <li><a href="/wiki/Boord_olefin_synthesis" title="Boord olefin synthesis">Boord olefin synthesis</a></li> <li><a href="/wiki/Chugaev_elimination" title="Chugaev elimination">Chugaev elimination</a></li> <li><a href="/wiki/Cope_reaction" title="Cope reaction">Cope reaction</a></li> <li><a href="/wiki/Corey%E2%80%93Winter_olefin_synthesis" title="Corey–Winter olefin synthesis">Corey–Winter olefin synthesis</a></li> <li><a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">Dehydrohalogenation</a></li> <li><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reaction</a></li> <li><a href="/wiki/Grieco_elimination" title="Grieco elimination">Grieco elimination</a></li> <li><a href="/wiki/Hofmann_elimination" title="Hofmann elimination">Hofmann elimination</a></li> <li><a href="/wiki/Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction" title="Horner–Wadsworth–Emmons reaction">Horner–Wadsworth–Emmons reaction</a></li> <li><a href="/wiki/Hydrazone_iodination" title="Hydrazone iodination">Hydrazone iodination</a></li> <li><a href="/wiki/Julia_olefination" title="Julia olefination">Julia olefination</a></li> <li><a href="/wiki/Julia%E2%80%93Kocienski_olefination" class="mw-redirect" title="Julia–Kocienski olefination">Julia–Kocienski olefination</a></li> <li><a href="/wiki/Kauffmann_olefination" title="Kauffmann olefination">Kauffmann olefination</a></li> <li><a href="/wiki/McMurry_reaction" title="McMurry reaction">McMurry reaction</a></li> <li><a href="/wiki/Peterson_olefination" title="Peterson olefination">Peterson olefination</a></li> <li><a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a></li> <li><a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a></li> <li><a href="/wiki/Takai_olefination" title="Takai olefination">Takai olefination</a></li> <li><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em">Carbon-heteroatom <br /> bond forming <br /> reactions</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azo_coupling" title="Azo coupling">Azo coupling</a></li> <li><a href="/wiki/Bartoli_indole_synthesis" title="Bartoli indole synthesis">Bartoli indole synthesis</a></li> <li><a href="/wiki/Boudouard_reaction" title="Boudouard reaction">Boudouard reaction</a></li> <li><a href="/wiki/Cadogan%E2%80%93Sundberg_indole_synthesis" title="Cadogan–Sundberg indole synthesis">Cadogan–Sundberg indole synthesis</a></li> <li><a href="/wiki/Diazonium_compound" title="Diazonium compound">Diazonium compound</a></li> <li><a href="/wiki/Esterification" class="mw-redirect" title="Esterification">Esterification</a></li> <li><a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagent</a></li> <li><a href="/wiki/Haloform_reaction" title="Haloform reaction">Haloform reaction</a></li> <li><a href="/wiki/Hegedus_indole_synthesis" title="Hegedus indole synthesis">Hegedus indole synthesis</a></li> <li><a href="/wiki/Hurd%E2%80%93Mori_1,2,3-thiadiazole_synthesis" title="Hurd–Mori 1,2,3-thiadiazole synthesis">Hurd–Mori 1,2,3-thiadiazole synthesis</a></li> <li><a href="/wiki/Kharasch%E2%80%93Sosnovsky_reaction" title="Kharasch–Sosnovsky reaction">Kharasch–Sosnovsky reaction</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Leimgruber%E2%80%93Batcho_indole_synthesis" title="Leimgruber–Batcho indole synthesis">Leimgruber–Batcho indole synthesis</a></li> <li><a href="/wiki/Mukaiyama_hydration" title="Mukaiyama hydration">Mukaiyama hydration</a></li> <li><a href="/wiki/Nenitzescu_indole_synthesis" title="Nenitzescu indole synthesis">Nenitzescu indole synthesis</a></li> <li><a href="/wiki/Oxymercuration_reaction" title="Oxymercuration reaction">Oxymercuration reaction</a></li> <li><a href="/wiki/Reed_reaction" title="Reed reaction">Reed reaction</a></li> <li><a href="/wiki/Schotten%E2%80%93Baumann_reaction" title="Schotten–Baumann reaction">Schotten–Baumann reaction</a></li> <li><a href="/wiki/Ullmann_condensation" title="Ullmann condensation">Ullmann condensation</a></li> <li><a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a></li> <li><a href="/wiki/Yamaguchi_esterification" title="Yamaguchi esterification">Yamaguchi esterification</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em">Degradation <br /> reactions</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Barbier%E2%80%93Wieland_degradation" title="Barbier–Wieland degradation">Barbier–Wieland degradation</a></li> <li><a href="/wiki/Bergmann_degradation" title="Bergmann degradation">Bergmann degradation</a></li> <li><a href="/wiki/Edman_degradation" title="Edman degradation">Edman degradation</a></li> <li><a href="/wiki/Emde_degradation" title="Emde degradation">Emde degradation</a></li> <li><a href="/wiki/Gallagher%E2%80%93Hollander_degradation" title="Gallagher–Hollander degradation">Gallagher–Hollander degradation</a></li> <li><a href="/wiki/Hofmann_rearrangement" title="Hofmann rearrangement">Hofmann rearrangement</a></li> <li><a href="/wiki/Hooker_reaction" title="Hooker reaction">Hooker reaction</a></li> <li><a href="/wiki/Isosaccharinic_acid" title="Isosaccharinic acid">Isosaccharinic acid</a></li> <li><a href="/wiki/Marker_degradation" title="Marker degradation">Marker degradation</a></li> <li><a href="/wiki/Ruff_degradation" title="Ruff degradation">Ruff degradation</a></li> <li><a href="/wiki/Strecker_degradation" title="Strecker degradation">Strecker degradation</a></li> <li><a href="/wiki/Von_Braun_amide_degradation" title="Von Braun amide degradation">Von Braun amide degradation</a></li> <li><a href="/wiki/Weerman_degradation" title="Weerman degradation">Weerman degradation</a></li> <li><a href="/wiki/Wohl_degradation" title="Wohl degradation">Wohl degradation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em"><a href="/wiki/Organic_redox_reaction" title="Organic redox reaction">Organic redox <br /> reactions</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyloin_condensation" title="Acyloin condensation">Acyloin condensation</a></li> <li><a href="/wiki/Adkins%E2%80%93Peterson_reaction" title="Adkins–Peterson reaction">Adkins–Peterson reaction</a></li> <li><a href="/wiki/Akabori_amino-acid_reaction" title="Akabori amino-acid reaction">Akabori amino-acid reaction</a></li> <li><a href="/wiki/Alcohol_oxidation" title="Alcohol oxidation">Alcohol oxidation</a></li> <li><a href="/wiki/Algar%E2%80%93Flynn%E2%80%93Oyamada_reaction" title="Algar–Flynn–Oyamada reaction">Algar–Flynn–Oyamada reaction</a></li> <li><a href="/wiki/Amide_reduction" title="Amide reduction">Amide reduction</a></li> <li><a href="/wiki/Andrussow_process" title="Andrussow process">Andrussow process</a></li> <li><a href="/wiki/Angeli%E2%80%93Rimini_reaction" title="Angeli–Rimini reaction">Angeli–Rimini reaction</a></li> <li><a href="/wiki/Aromatization" title="Aromatization">Aromatization</a></li> <li><a href="/wiki/Autoxidation" title="Autoxidation">Autoxidation</a></li> <li><a href="/wiki/Baeyer%E2%80%93Villiger_oxidation" title="Baeyer–Villiger oxidation">Baeyer–Villiger oxidation</a></li> <li><a href="/wiki/Barton%E2%80%93McCombie_deoxygenation" title="Barton–McCombie deoxygenation">Barton–McCombie deoxygenation</a></li> <li><a href="/wiki/Bechamp_reduction" class="mw-redirect" title="Bechamp reduction">Bechamp reduction</a></li> <li><a href="/wiki/Benkeser_reaction" class="mw-redirect" title="Benkeser reaction">Benkeser reaction</a></li> <li><a href="/wiki/Bergmann_degradation" title="Bergmann degradation">Bergmann degradation</a></li> <li><a href="/wiki/Birch_reduction" title="Birch reduction">Birch reduction</a></li> <li><a href="/wiki/Bohn%E2%80%93Schmidt_reaction" title="Bohn–Schmidt reaction">Bohn–Schmidt reaction</a></li> <li><a href="/wiki/Bosch_reaction" title="Bosch reaction">Bosch reaction</a></li> <li><a href="/wiki/Bouveault%E2%80%93Blanc_reduction" title="Bouveault–Blanc reduction">Bouveault–Blanc reduction</a></li> <li><a href="/wiki/Boyland%E2%80%93Sims_oxidation" title="Boyland–Sims oxidation">Boyland–Sims oxidation</a></li> <li><a href="/wiki/Cannizzaro_reaction" title="Cannizzaro reaction">Cannizzaro reaction</a></li> <li><a href="/wiki/Carbonyl_reduction" title="Carbonyl reduction">Carbonyl reduction</a></li> <li><a href="/wiki/Clemmensen_reduction" title="Clemmensen reduction">Clemmensen reduction</a></li> <li><a href="/wiki/Collins_oxidation" title="Collins oxidation">Collins oxidation</a></li> <li><a href="/wiki/Corey%E2%80%93Itsuno_reduction" title="Corey–Itsuno reduction">Corey–Itsuno reduction</a></li> <li><a href="/wiki/Corey%E2%80%93Kim_oxidation" title="Corey–Kim oxidation">Corey–Kim oxidation</a></li> <li><a href="/wiki/Corey%E2%80%93Winter_olefin_synthesis" title="Corey–Winter olefin synthesis">Corey–Winter olefin synthesis</a></li> <li><a href="/wiki/Criegee_oxidation" title="Criegee oxidation">Criegee oxidation</a></li> <li><a href="/wiki/Dakin_oxidation" title="Dakin oxidation">Dakin oxidation</a></li> <li><a href="/wiki/Davis_oxidation" title="Davis oxidation">Davis oxidation</a></li> <li><a href="/wiki/Deoxygenation" title="Deoxygenation">Deoxygenation</a></li> <li><a href="/wiki/Dess%E2%80%93Martin_oxidation" title="Dess–Martin oxidation">Dess–Martin oxidation</a></li> <li><a href="/wiki/DNA_oxidation" title="DNA oxidation">DNA oxidation</a></li> <li><a href="/wiki/Elbs_persulfate_oxidation" title="Elbs persulfate oxidation">Elbs persulfate oxidation</a></li> <li><a href="/wiki/Emde_degradation" title="Emde degradation">Emde degradation</a></li> <li><a href="/wiki/Eschweiler%E2%80%93Clarke_reaction" title="Eschweiler–Clarke reaction">Eschweiler–Clarke reaction</a></li> <li><a href="/wiki/%C3%89tard_reaction" title="Étard reaction">Étard reaction</a></li> <li><a href="/wiki/Fischer%E2%80%93Tropsch_process" title="Fischer–Tropsch process">Fischer–Tropsch process</a></li> <li><a href="/wiki/Fleming%E2%80%93Tamao_oxidation" title="Fleming–Tamao oxidation">Fleming–Tamao oxidation</a></li> <li><a href="/wiki/Fukuyama_reduction" title="Fukuyama reduction">Fukuyama reduction</a></li> <li><a href="/wiki/Ganem_oxidation" title="Ganem oxidation">Ganem oxidation</a></li> <li><a href="/wiki/Glycol_cleavage" title="Glycol cleavage">Glycol cleavage</a></li> <li><a href="/wiki/Griesbaum_coozonolysis" title="Griesbaum coozonolysis">Griesbaum coozonolysis</a></li> <li><a href="/wiki/Grundmann_aldehyde_synthesis" title="Grundmann aldehyde synthesis">Grundmann aldehyde synthesis</a></li> <li><a href="/wiki/Haloform_reaction" title="Haloform reaction">Haloform reaction</a></li> <li><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a></li> <li><a href="/wiki/Hydrogenolysis" title="Hydrogenolysis">Hydrogenolysis</a></li> <li><a href="/wiki/Hydroxylation" title="Hydroxylation">Hydroxylation</a></li> <li><a href="/wiki/Jones_oxidation" title="Jones oxidation">Jones oxidation</a></li> <li><a href="/wiki/Kiliani%E2%80%93Fischer_synthesis" title="Kiliani–Fischer synthesis">Kiliani–Fischer synthesis</a></li> <li><a href="/wiki/Kolbe_electrolysis" title="Kolbe electrolysis">Kolbe electrolysis</a></li> <li><a href="/wiki/Kornblum_oxidation" title="Kornblum oxidation">Kornblum oxidation</a></li> <li><a href="/wiki/Kornblum%E2%80%93DeLaMare_rearrangement" title="Kornblum–DeLaMare rearrangement">Kornblum–DeLaMare rearrangement</a></li> <li><a href="/wiki/Leuckart_reaction" title="Leuckart reaction">Leuckart reaction</a></li> <li><a href="/wiki/Ley_oxidation" class="mw-redirect" title="Ley oxidation">Ley oxidation</a></li> <li><a href="/wiki/Lindgren_oxidation" title="Lindgren oxidation">Lindgren oxidation</a></li> <li><a href="/wiki/Lipid_peroxidation" title="Lipid peroxidation">Lipid peroxidation</a></li> <li><a href="/wiki/Lombardo_methylenation" title="Lombardo methylenation">Lombardo methylenation</a></li> <li><a href="/wiki/Luche_reduction" title="Luche reduction">Luche reduction</a></li> <li><a href="/wiki/Mark%C3%B3%E2%80%93Lam_deoxygenation" title="Markó–Lam deoxygenation">Markó–Lam deoxygenation</a></li> <li><a href="/wiki/McFadyen%E2%80%93Stevens_reaction" title="McFadyen–Stevens reaction">McFadyen–Stevens reaction</a></li> <li><a href="/wiki/Meerwein%E2%80%93Ponndorf%E2%80%93Verley_reduction" title="Meerwein–Ponndorf–Verley reduction">Meerwein–Ponndorf–Verley reduction</a></li> <li><a href="/wiki/Methionine_sulfoxide" title="Methionine sulfoxide">Methionine sulfoxide</a></li> <li><a href="/wiki/Miyaura_borylation" title="Miyaura borylation">Miyaura borylation</a></li> <li><a href="/wiki/Mozingo_reduction" title="Mozingo reduction">Mozingo reduction</a></li> <li><a href="/wiki/Noyori_asymmetric_hydrogenation" class="mw-redirect" title="Noyori asymmetric hydrogenation">Noyori asymmetric hydrogenation</a></li> <li><a href="/wiki/Omega_oxidation" title="Omega oxidation">Omega oxidation</a></li> <li><a href="/wiki/Oppenauer_oxidation" title="Oppenauer oxidation">Oppenauer oxidation</a></li> <li><a href="/wiki/Oxygen_rebound_mechanism" title="Oxygen rebound mechanism">Oxygen rebound mechanism</a></li> <li><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a></li> <li><a href="/wiki/Parikh%E2%80%93Doering_oxidation" title="Parikh–Doering oxidation">Parikh–Doering oxidation</a></li> <li><a href="/wiki/Pinnick_oxidation" title="Pinnick oxidation">Pinnick oxidation</a></li> <li><a href="/wiki/Pr%C3%A9vost_reaction" title="Prévost reaction">Prévost reaction</a></li> <li><a href="/wiki/Reduction_of_nitro_compounds" title="Reduction of nitro compounds">Reduction of nitro compounds</a></li> <li><a href="/wiki/Reductive_amination" title="Reductive amination">Reductive amination</a></li> <li><a href="/wiki/Riley_oxidation" title="Riley oxidation">Riley oxidation</a></li> <li><a href="/wiki/Rosenmund_reduction" title="Rosenmund reduction">Rosenmund reduction</a></li> <li><a href="/wiki/Rubottom_oxidation" title="Rubottom oxidation">Rubottom oxidation</a></li> <li><a href="/wiki/Sabatier_reaction" title="Sabatier reaction">Sabatier reaction</a></li> <li><a href="/wiki/Sarett_oxidation" title="Sarett oxidation">Sarett oxidation</a></li> <li><a href="/wiki/Selenoxide_elimination" title="Selenoxide elimination">Selenoxide elimination</a></li> <li><a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a></li> <li><a href="/wiki/Sharpless_asymmetric_dihydroxylation" title="Sharpless asymmetric dihydroxylation">Sharpless asymmetric dihydroxylation</a></li> <li><a href="/wiki/Epoxidation_of_allylic_alcohols" title="Epoxidation of allylic alcohols">Epoxidation of allylic alcohols</a></li> <li><a href="/wiki/Sharpless_epoxidation" title="Sharpless epoxidation">Sharpless epoxidation</a></li> <li><a href="/wiki/Sharpless_oxyamination" title="Sharpless oxyamination">Sharpless oxyamination</a></li> <li><a href="/wiki/Stahl_oxidation" title="Stahl oxidation">Stahl oxidation</a></li> <li><a href="/wiki/Staudinger_reaction" title="Staudinger reaction">Staudinger reaction</a></li> <li><a href="/wiki/Stephen_aldehyde_synthesis" title="Stephen aldehyde synthesis">Stephen aldehyde synthesis</a></li> <li><a href="/wiki/Swern_oxidation" title="Swern oxidation">Swern oxidation</a></li> <li><a href="/wiki/Transfer_hydrogenation" title="Transfer hydrogenation">Transfer hydrogenation</a></li> <li><a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a></li> <li><a href="/wiki/Wharton_reaction" title="Wharton reaction">Wharton reaction</a></li> <li><a href="/wiki/Whiting_reaction" title="Whiting reaction">Whiting reaction</a></li> <li><a href="/wiki/Wohl%E2%80%93Aue_reaction" title="Wohl–Aue reaction">Wohl–Aue reaction</a></li> <li><a href="/wiki/Wolff%E2%80%93Kishner_reduction" title="Wolff–Kishner reduction">Wolff–Kishner reduction</a></li> <li><a href="/wiki/Wolffenstein%E2%80%93B%C3%B6ters_reaction" title="Wolffenstein–Böters reaction">Wolffenstein–Böters reaction</a></li> <li><a href="/wiki/Zinin_reaction" title="Zinin reaction">Zinin reaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em"><a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">Rearrangement <br /> reactions</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,2-rearrangement" title="1,2-rearrangement">1,2-rearrangement</a></li> <li><a href="/wiki/1,2-Wittig_rearrangement" title="1,2-Wittig rearrangement">1,2-Wittig rearrangement</a></li> <li><a href="/wiki/2,3-sigmatropic_rearrangement" title="2,3-sigmatropic rearrangement">2,3-sigmatropic rearrangement</a></li> <li><a href="/wiki/2,3-Wittig_rearrangement" title="2,3-Wittig rearrangement">2,3-Wittig rearrangement</a></li> <li><a href="/wiki/Achmatowicz_reaction" title="Achmatowicz reaction">Achmatowicz reaction</a></li> <li><a href="/wiki/Alkyne_zipper_reaction" title="Alkyne zipper reaction">Alkyne zipper reaction</a></li> <li><a href="/wiki/Allen%E2%80%93Millar%E2%80%93Trippett_rearrangement" title="Allen–Millar–Trippett rearrangement">Allen–Millar–Trippett rearrangement</a></li> <li><a href="/wiki/Allylic_rearrangement" title="Allylic rearrangement">Allylic rearrangement</a></li> <li><a href="/wiki/Alpha-ketol_rearrangement" class="mw-redirect" title="Alpha-ketol rearrangement">Alpha-ketol rearrangement</a></li> <li><a href="/wiki/Amadori_rearrangement" title="Amadori rearrangement">Amadori rearrangement</a></li> <li><a href="/wiki/Arndt%E2%80%93Eistert_reaction" title="Arndt–Eistert reaction">Arndt–Eistert reaction</a></li> <li><a href="/wiki/Aza-Cope_rearrangement" title="Aza-Cope rearrangement">Aza-Cope rearrangement</a></li> <li><a href="/wiki/Baker%E2%80%93Venkataraman_rearrangement" title="Baker–Venkataraman rearrangement">Baker–Venkataraman rearrangement</a></li> <li><a href="/wiki/Bamberger_rearrangement" title="Bamberger rearrangement">Bamberger rearrangement</a></li> <li><a href="/wiki/Banert_cascade" title="Banert cascade">Banert cascade</a></li> <li><a href="/wiki/Beckmann_rearrangement" title="Beckmann rearrangement">Beckmann rearrangement</a></li> <li><a href="/wiki/Benzilic_acid_rearrangement" title="Benzilic acid rearrangement">Benzilic acid rearrangement</a></li> <li><a href="/wiki/Bergman_cyclization" title="Bergman cyclization">Bergman cyclization</a></li> <li><a href="/wiki/Bergmann_degradation" title="Bergmann degradation">Bergmann degradation</a></li> <li><a href="/wiki/Boekelheide_reaction" title="Boekelheide reaction">Boekelheide reaction</a></li> <li><a href="/wiki/Brook_rearrangement" title="Brook rearrangement">Brook rearrangement</a></li> <li><a href="/wiki/Buchner_ring_expansion" title="Buchner ring expansion">Buchner ring expansion</a></li> <li><a href="/wiki/Carroll_rearrangement" title="Carroll rearrangement">Carroll rearrangement</a></li> <li><a href="/wiki/Chan_rearrangement" title="Chan rearrangement">Chan rearrangement</a></li> <li><a href="/wiki/Claisen_rearrangement" title="Claisen rearrangement">Claisen rearrangement</a></li> <li><a href="/wiki/Cope_rearrangement" title="Cope rearrangement">Cope rearrangement</a></li> <li><a href="/wiki/Corey%E2%80%93Fuchs_reaction" title="Corey–Fuchs reaction">Corey–Fuchs reaction</a></li> <li><a href="/wiki/Cornforth_rearrangement" title="Cornforth rearrangement">Cornforth rearrangement</a></li> <li><a href="/wiki/Criegee_rearrangement" title="Criegee rearrangement">Criegee rearrangement</a></li> <li><a href="/wiki/Curtius_rearrangement" title="Curtius rearrangement">Curtius rearrangement</a></li> <li><a href="/wiki/Demjanov_rearrangement" title="Demjanov rearrangement">Demjanov rearrangement</a></li> <li><a href="/wiki/Di-%CF%80-methane_rearrangement" title="Di-π-methane rearrangement">Di-π-methane rearrangement</a></li> <li><a href="/wiki/Dimroth_rearrangement" title="Dimroth rearrangement">Dimroth rearrangement</a></li> <li><a href="/wiki/Divinylcyclopropane-cycloheptadiene_rearrangement" title="Divinylcyclopropane-cycloheptadiene rearrangement">Divinylcyclopropane-cycloheptadiene rearrangement</a></li> <li><a href="/wiki/Dowd%E2%80%93Beckwith_ring-expansion_reaction" title="Dowd–Beckwith ring-expansion reaction">Dowd–Beckwith ring-expansion reaction</a></li> <li><a href="/wiki/Electrocyclic_reaction" title="Electrocyclic reaction">Electrocyclic reaction</a></li> <li><a href="/wiki/Ene_reaction" title="Ene reaction">Ene reaction</a></li> <li><a href="/wiki/Enyne_metathesis" title="Enyne metathesis">Enyne metathesis</a></li> <li><a href="/wiki/Favorskii_reaction" title="Favorskii reaction">Favorskii reaction</a></li> <li><a href="/wiki/Favorskii_rearrangement" title="Favorskii rearrangement">Favorskii rearrangement</a></li> <li><a href="/wiki/Ferrier_carbocyclization" title="Ferrier carbocyclization">Ferrier carbocyclization</a></li> <li><a href="/wiki/Ferrier_rearrangement" title="Ferrier rearrangement">Ferrier rearrangement</a></li> <li><a href="/wiki/Fischer%E2%80%93Hepp_rearrangement" title="Fischer–Hepp rearrangement">Fischer–Hepp rearrangement</a></li> <li><a href="/wiki/Fries_rearrangement" title="Fries rearrangement">Fries rearrangement</a></li> <li><a href="/wiki/Fritsch%E2%80%93Buttenberg%E2%80%93Wiechell_rearrangement" title="Fritsch–Buttenberg–Wiechell rearrangement">Fritsch–Buttenberg–Wiechell rearrangement</a></li> <li><a href="/wiki/Gabriel%E2%80%93Colman_rearrangement" title="Gabriel–Colman rearrangement">Gabriel–Colman rearrangement</a></li> <li><a href="/wiki/Group_transfer_reaction" title="Group transfer reaction">Group transfer reaction</a></li> <li><a href="/wiki/Halogen_dance_rearrangement" title="Halogen dance rearrangement">Halogen dance rearrangement</a></li> <li><a href="/wiki/Hayashi_rearrangement" title="Hayashi rearrangement">Hayashi rearrangement</a></li> <li><a href="/wiki/Hofmann_rearrangement" title="Hofmann rearrangement">Hofmann rearrangement</a></li> <li><a href="/wiki/Hofmann%E2%80%93Martius_rearrangement" title="Hofmann–Martius rearrangement">Hofmann–Martius rearrangement</a></li> <li><a href="/wiki/Ireland%E2%80%93Claisen_rearrangement" title="Ireland–Claisen rearrangement">Ireland–Claisen rearrangement</a></li> <li><a href="/wiki/Jacobsen_rearrangement" title="Jacobsen rearrangement">Jacobsen rearrangement</a></li> <li><a href="/wiki/Kornblum%E2%80%93DeLaMare_rearrangement" title="Kornblum–DeLaMare rearrangement">Kornblum–DeLaMare rearrangement</a></li> <li><a href="/wiki/Kowalski_ester_homologation" title="Kowalski ester homologation">Kowalski ester homologation</a></li> <li><a href="/wiki/Lobry_de_Bruyn%E2%80%93Van_Ekenstein_transformation" title="Lobry de Bruyn–Van Ekenstein transformation">Lobry de Bruyn–Van Ekenstein transformation</a></li> <li><a href="/wiki/Lossen_rearrangement" title="Lossen rearrangement">Lossen rearrangement</a></li> <li><a href="/wiki/McFadyen%E2%80%93Stevens_reaction" title="McFadyen–Stevens reaction">McFadyen–Stevens reaction</a></li> <li><a href="/wiki/McLafferty_rearrangement" title="McLafferty rearrangement">McLafferty rearrangement</a></li> <li><a href="/wiki/Meyer%E2%80%93Schuster_rearrangement" title="Meyer–Schuster rearrangement">Meyer–Schuster rearrangement</a></li> <li><a href="/wiki/Mislow%E2%80%93Evans_rearrangement" title="Mislow–Evans rearrangement">Mislow–Evans rearrangement</a></li> <li><a href="/wiki/Mumm_rearrangement" title="Mumm rearrangement">Mumm rearrangement</a></li> <li><a href="/wiki/Myers_allene_synthesis" title="Myers allene synthesis">Myers allene synthesis</a></li> <li><a href="/wiki/Nazarov_cyclization_reaction" title="Nazarov cyclization reaction">Nazarov cyclization reaction</a></li> <li><a href="/wiki/Neber_rearrangement" title="Neber rearrangement">Neber rearrangement</a></li> <li><a href="/wiki/Newman%E2%80%93Kwart_rearrangement" title="Newman–Kwart rearrangement">Newman–Kwart rearrangement</a></li> <li><a href="/wiki/Overman_rearrangement" title="Overman rearrangement">Overman rearrangement</a></li> <li><a href="/wiki/Oxy-Cope_rearrangement" title="Oxy-Cope rearrangement">Oxy-Cope rearrangement</a></li> <li><a href="/wiki/Pericyclic_reaction" title="Pericyclic reaction">Pericyclic reaction</a></li> <li><a href="/wiki/Piancatelli_rearrangement" title="Piancatelli rearrangement">Piancatelli rearrangement</a></li> <li><a href="/wiki/Pinacol_rearrangement" title="Pinacol rearrangement">Pinacol rearrangement</a></li> <li><a href="/wiki/Pummerer_rearrangement" title="Pummerer rearrangement">Pummerer rearrangement</a></li> <li><a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a></li> <li><a href="/wiki/Ring_expansion_and_contraction" title="Ring expansion and contraction">Ring expansion and contraction</a></li> <li><a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">Ring-closing metathesis</a></li> <li><a href="/wiki/Rupe_reaction" class="mw-redirect" title="Rupe reaction">Rupe reaction</a></li> <li><a href="/wiki/Schmidt_reaction" title="Schmidt reaction">Schmidt reaction</a></li> <li><a href="/wiki/Semipinacol_rearrangement" title="Semipinacol rearrangement">Semipinacol rearrangement</a></li> <li><a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a></li> <li><a href="/wiki/Sigmatropic_reaction" title="Sigmatropic reaction">Sigmatropic reaction</a></li> <li><a href="/wiki/Skatteb%C3%B8l_rearrangement" title="Skattebøl rearrangement">Skattebøl rearrangement</a></li> <li><a href="/wiki/Smiles_rearrangement" title="Smiles rearrangement">Smiles rearrangement</a></li> <li><a href="/wiki/Sommelet%E2%80%93Hauser_rearrangement" title="Sommelet–Hauser rearrangement">Sommelet–Hauser rearrangement</a></li> <li><a href="/wiki/Stevens_rearrangement" title="Stevens rearrangement">Stevens rearrangement</a></li> <li><a href="/wiki/Stieglitz_rearrangement" title="Stieglitz rearrangement">Stieglitz rearrangement</a></li> <li><a href="/wiki/Thermal_rearrangement_of_aromatic_hydrocarbons" title="Thermal rearrangement of aromatic hydrocarbons">Thermal rearrangement of aromatic hydrocarbons</a></li> <li><a href="/wiki/Tiffeneau%E2%80%93Demjanov_rearrangement" title="Tiffeneau–Demjanov rearrangement">Tiffeneau–Demjanov rearrangement</a></li> <li><a href="/wiki/Vinylcyclopropane_rearrangement" title="Vinylcyclopropane rearrangement">Vinylcyclopropane rearrangement</a></li> <li><a href="/wiki/Wagner%E2%80%93Meerwein_rearrangement" title="Wagner–Meerwein rearrangement">Wagner–Meerwein rearrangement</a></li> <li><a href="/wiki/Wallach_rearrangement" title="Wallach rearrangement">Wallach rearrangement</a></li> <li><a href="/wiki/Weerman_degradation" title="Weerman degradation">Weerman degradation</a></li> <li><a href="/wiki/Westphalen%E2%80%93Lettr%C3%A9_rearrangement" title="Westphalen–Lettré rearrangement">Westphalen–Lettré rearrangement</a></li> <li><a href="/wiki/Willgerodt_rearrangement" title="Willgerodt rearrangement">Willgerodt rearrangement</a></li> <li><a href="/wiki/Wolff_rearrangement" title="Wolff rearrangement">Wolff rearrangement</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em"><a href="/wiki/Ring_forming_reaction" title="Ring forming reaction">Ring forming <br /> reactions</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,3-Dipolar_cycloaddition" title="1,3-Dipolar cycloaddition">1,3-Dipolar cycloaddition</a></li> <li><a href="/wiki/Annulation" title="Annulation">Annulation</a></li> <li><a href="/wiki/Azide-alkyne_Huisgen_cycloaddition" title="Azide-alkyne Huisgen cycloaddition">Azide-alkyne Huisgen cycloaddition</a></li> <li><a href="/wiki/Baeyer%E2%80%93Emmerling_indole_synthesis" title="Baeyer–Emmerling indole synthesis">Baeyer–Emmerling indole synthesis</a></li> <li><a href="/wiki/Bartoli_indole_synthesis" title="Bartoli indole synthesis">Bartoli indole synthesis</a></li> <li><a href="/wiki/Bergman_cyclization" title="Bergman cyclization">Bergman cyclization</a></li> <li><a href="/wiki/Biginelli_reaction" title="Biginelli reaction">Biginelli reaction</a></li> <li><a href="/wiki/Bischler%E2%80%93M%C3%B6hlau_indole_synthesis" title="Bischler–Möhlau indole synthesis">Bischler–Möhlau indole synthesis</a></li> <li><a href="/wiki/Bischler%E2%80%93Napieralski_reaction" title="Bischler–Napieralski reaction">Bischler–Napieralski reaction</a></li> <li><a href="/wiki/Blum%E2%80%93Ittah_aziridine_synthesis" title="Blum–Ittah aziridine synthesis">Blum–Ittah aziridine synthesis</a></li> <li><a href="/wiki/Bobbitt_reaction" title="Bobbitt reaction">Bobbitt reaction</a></li> <li><a href="/wiki/Bohlmann%E2%80%93Rahtz_pyridine_synthesis" title="Bohlmann–Rahtz pyridine synthesis">Bohlmann–Rahtz pyridine synthesis</a></li> <li><a href="/wiki/Borsche%E2%80%93Drechsel_cyclization" title="Borsche–Drechsel cyclization">Borsche–Drechsel cyclization</a></li> <li><a href="/wiki/Bucherer_carbazole_synthesis" title="Bucherer carbazole synthesis">Bucherer carbazole synthesis</a></li> <li><a href="/wiki/Bucherer%E2%80%93Bergs_reaction" title="Bucherer–Bergs reaction">Bucherer–Bergs reaction</a></li> <li><a href="/wiki/Cadogan%E2%80%93Sundberg_indole_synthesis" title="Cadogan–Sundberg indole synthesis">Cadogan–Sundberg indole synthesis</a></li> <li><a href="/wiki/Camps_quinoline_synthesis" title="Camps quinoline synthesis">Camps quinoline synthesis</a></li> <li><a href="/wiki/Chichibabin_pyridine_synthesis" title="Chichibabin pyridine synthesis">Chichibabin pyridine synthesis</a></li> <li><a href="/wiki/Cook%E2%80%93Heilbron_thiazole_synthesis" title="Cook–Heilbron thiazole synthesis">Cook–Heilbron thiazole synthesis</a></li> <li><a href="/wiki/Cycloaddition" title="Cycloaddition">Cycloaddition</a></li> <li><a href="/wiki/Darzens_reaction" title="Darzens reaction">Darzens reaction</a></li> <li><a href="/wiki/Davis%E2%80%93Beirut_reaction" title="Davis–Beirut reaction">Davis–Beirut reaction</a></li> <li><a href="/wiki/De_Kimpe_aziridine_synthesis" title="De Kimpe aziridine synthesis">De Kimpe aziridine synthesis</a></li> <li><a href="/wiki/Debus%E2%80%93Radziszewski_imidazole_synthesis" title="Debus–Radziszewski imidazole synthesis">Debus–Radziszewski imidazole synthesis</a></li> <li><a href="/wiki/Dieckmann_condensation" title="Dieckmann condensation">Dieckmann condensation</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Feist%E2%80%93Benary_synthesis" title="Feist–Benary synthesis">Feist–Benary synthesis</a></li> <li><a href="/wiki/Ferrario%E2%80%93Ackermann_reaction" title="Ferrario–Ackermann reaction">Ferrario–Ackermann reaction</a></li> <li><a href="/wiki/Fiesselmann_thiophene_synthesis" title="Fiesselmann thiophene synthesis">Fiesselmann thiophene synthesis</a></li> <li><a href="/wiki/Fischer_indole_synthesis" title="Fischer indole synthesis">Fischer indole synthesis</a></li> <li><a href="/wiki/Fischer_oxazole_synthesis" title="Fischer oxazole synthesis">Fischer oxazole synthesis</a></li> <li><a href="/wiki/Friedl%C3%A4nder_synthesis" title="Friedländer synthesis">Friedländer synthesis</a></li> <li><a href="/wiki/Gewald_reaction" title="Gewald reaction">Gewald reaction</a></li> <li><a href="/wiki/Graham_reaction" title="Graham reaction">Graham reaction</a></li> <li><a href="/wiki/Hantzsch_pyridine_synthesis" title="Hantzsch pyridine synthesis">Hantzsch pyridine synthesis</a></li> <li><a href="/wiki/Hegedus_indole_synthesis" title="Hegedus indole synthesis">Hegedus indole synthesis</a></li> <li><a href="/wiki/Hemetsberger_indole_synthesis" title="Hemetsberger indole synthesis">Hemetsberger indole synthesis</a></li> <li><a href="/wiki/Hofmann%E2%80%93L%C3%B6ffler_reaction" title="Hofmann–Löffler reaction">Hofmann–Löffler reaction</a></li> <li><a href="/wiki/Hurd%E2%80%93Mori_1,2,3-thiadiazole_synthesis" title="Hurd–Mori 1,2,3-thiadiazole synthesis">Hurd–Mori 1,2,3-thiadiazole synthesis</a></li> <li><a href="/wiki/Iodolactonization" title="Iodolactonization">Iodolactonization</a></li> <li><a href="/wiki/Isay_reaction" title="Isay reaction">Isay reaction</a></li> <li><a href="/wiki/Jacobsen_epoxidation" title="Jacobsen epoxidation">Jacobsen epoxidation</a></li> <li><a href="/wiki/Johnson%E2%80%93Corey%E2%80%93Chaykovsky_reaction" title="Johnson–Corey–Chaykovsky reaction">Johnson–Corey–Chaykovsky reaction</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Knorr_quinoline_synthesis" title="Knorr quinoline synthesis">Knorr quinoline synthesis</a></li> <li><a href="/wiki/Kr%C3%B6hnke_pyridine_synthesis" title="Kröhnke pyridine synthesis">Kröhnke pyridine synthesis</a></li> <li><a href="/wiki/Kulinkovich_reaction" title="Kulinkovich reaction">Kulinkovich reaction</a></li> <li><a href="/wiki/Larock_indole_synthesis" title="Larock indole synthesis">Larock indole synthesis</a></li> <li><a href="/wiki/Madelung_synthesis" title="Madelung synthesis">Madelung synthesis</a></li> <li><a href="/wiki/Nazarov_cyclization_reaction" title="Nazarov cyclization reaction">Nazarov cyclization reaction</a></li> <li><a href="/wiki/Nenitzescu_indole_synthesis" title="Nenitzescu indole synthesis">Nenitzescu indole synthesis</a></li> <li><a href="/wiki/Niementowski_quinazoline_synthesis" title="Niementowski quinazoline synthesis">Niementowski quinazoline synthesis</a></li> <li><a href="/wiki/Niementowski_quinoline_synthesis" title="Niementowski quinoline synthesis">Niementowski quinoline synthesis</a></li> <li><a href="/wiki/Paal%E2%80%93Knorr_synthesis" title="Paal–Knorr synthesis">Paal–Knorr synthesis</a></li> <li><a href="/wiki/Patern%C3%B2%E2%80%93B%C3%BCchi_reaction" title="Paternò–Büchi reaction">Paternò–Büchi reaction</a></li> <li><a href="/wiki/Pechmann_condensation" title="Pechmann condensation">Pechmann condensation</a></li> <li><a href="/wiki/Petrenko-Kritschenko_piperidone_synthesis" title="Petrenko-Kritschenko piperidone synthesis">Petrenko-Kritschenko piperidone synthesis</a></li> <li><a href="/wiki/Pictet%E2%80%93Spengler_reaction" title="Pictet–Spengler reaction">Pictet–Spengler reaction</a></li> <li><a href="/wiki/Pomeranz%E2%80%93Fritsch_reaction" title="Pomeranz–Fritsch reaction">Pomeranz–Fritsch reaction</a></li> <li><a href="/wiki/Prilezhaev_reaction" title="Prilezhaev reaction">Prilezhaev reaction</a></li> <li><a href="/wiki/Pschorr_cyclization" title="Pschorr cyclization">Pschorr cyclization</a></li> <li><a href="/wiki/Reissert_indole_synthesis" title="Reissert indole synthesis">Reissert indole synthesis</a></li> <li><a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">Ring-closing metathesis</a></li> <li><a href="/wiki/Robinson_annulation" title="Robinson annulation">Robinson annulation</a></li> <li><a href="/wiki/Sharpless_epoxidation" title="Sharpless epoxidation">Sharpless epoxidation</a></li> <li><a href="/wiki/Simmons%E2%80%93Smith_reaction" title="Simmons–Smith reaction">Simmons–Smith reaction</a></li> <li><a href="/wiki/Skraup_reaction" title="Skraup reaction">Skraup reaction</a></li> <li><a href="/wiki/Urech_hydantoin_synthesis" title="Urech hydantoin synthesis">Urech hydantoin synthesis</a></li> <li><a href="/wiki/Van_Leusen_reaction" title="Van Leusen reaction">Van Leusen reaction</a></li> <li><a href="/wiki/Wenker_synthesis" title="Wenker synthesis">Wenker synthesis</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cycloaddition" title="Cycloaddition">Cycloaddition</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,3-Dipolar_cycloaddition" title="1,3-Dipolar cycloaddition">1,3-Dipolar cycloaddition</a></li> <li><a href="/wiki/4%2B4_Photocycloaddition" title="4+4 Photocycloaddition">4+4 Photocycloaddition</a></li> <li><a href="/wiki/(4%2B3)_cycloaddition" title="(4+3) cycloaddition">(4+3) cycloaddition</a></li> <li><a href="/wiki/6%2B4_Cycloaddition" title="6+4 Cycloaddition">6+4 Cycloaddition</a></li> <li><a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Alkyne trimerisation</a></li> <li><a href="/wiki/Aza-Diels%E2%80%93Alder_reaction" title="Aza-Diels–Alder reaction">Aza-Diels–Alder reaction</a></li> <li><a href="/wiki/Azide-alkyne_Huisgen_cycloaddition" title="Azide-alkyne Huisgen cycloaddition">Azide-alkyne Huisgen cycloaddition</a></li> <li><a href="/wiki/Bradsher_cycloaddition" title="Bradsher cycloaddition">Bradsher cycloaddition</a></li> <li><a href="/wiki/Cheletropic_reaction" title="Cheletropic reaction">Cheletropic reaction</a></li> <li><a href="/wiki/Conia-ene_reaction" title="Conia-ene reaction">Conia-ene reaction</a></li> <li><a href="/wiki/Cyclopropanation" title="Cyclopropanation">Cyclopropanation</a></li> <li><a href="/wiki/Diazoalkane_1,3-dipolar_cycloaddition" title="Diazoalkane 1,3-dipolar cycloaddition">Diazoalkane 1,3-dipolar cycloaddition</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Enone%E2%80%93alkene_cycloadditions" title="Enone–alkene cycloadditions">Enone–alkene cycloadditions</a></li> <li><a href="/wiki/Hexadehydro_Diels%E2%80%93Alder_reaction" title="Hexadehydro Diels–Alder reaction">Hexadehydro Diels–Alder reaction</a></li> <li><a href="/wiki/Intramolecular_Diels%E2%80%93Alder_cycloaddition" title="Intramolecular Diels–Alder cycloaddition">Intramolecular Diels–Alder cycloaddition</a></li> <li><a href="/wiki/Inverse_electron-demand_Diels%E2%80%93Alder_reaction" title="Inverse electron-demand Diels–Alder reaction">Inverse electron-demand Diels–Alder reaction</a></li> <li><a href="/wiki/Ketene_cycloaddition" title="Ketene cycloaddition">Ketene cycloaddition</a></li> <li><a href="/wiki/McCormack_reaction" title="McCormack reaction">McCormack reaction</a></li> <li><a href="/wiki/Metal-centered_cycloaddition_reactions" title="Metal-centered cycloaddition reactions">Metal-centered cycloaddition reactions</a></li> <li><a href="/wiki/Nitrone-olefin_(3%2B2)_cycloaddition" title="Nitrone-olefin (3+2) cycloaddition">Nitrone-olefin (3+2) cycloaddition</a></li> <li><a href="/wiki/Oxo-Diels%E2%80%93Alder_reaction" title="Oxo-Diels–Alder reaction">Oxo-Diels–Alder reaction</a></li> <li><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a></li> <li><a href="/wiki/Pauson%E2%80%93Khand_reaction" title="Pauson–Khand reaction">Pauson–Khand reaction</a></li> <li><a href="/wiki/Povarov_reaction" title="Povarov reaction">Povarov reaction</a></li> <li><a href="/wiki/Prato_reaction" title="Prato reaction">Prato reaction</a></li> <li><a href="/wiki/Retro-Diels%E2%80%93Alder_reaction" title="Retro-Diels–Alder reaction">Retro-Diels–Alder reaction</a></li> <li><a href="/wiki/Staudinger_synthesis" title="Staudinger synthesis">Staudinger synthesis</a></li> <li><a href="/wiki/Trimethylenemethane_cycloaddition" title="Trimethylenemethane cycloaddition">Trimethylenemethane cycloaddition</a></li> <li><a href="/wiki/Vinylcyclopropane_(5%2B2)_cycloaddition" title="Vinylcyclopropane (5+2) cycloaddition">Vinylcyclopropane (5+2) cycloaddition</a></li> <li><a href="/wiki/Wagner-Jauregg_reaction" title="Wagner-Jauregg reaction">Wagner-Jauregg reaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Heterocycle forming reactions</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Algar%E2%80%93Flynn%E2%80%93Oyamada_reaction" title="Algar–Flynn–Oyamada reaction">Algar–Flynn–Oyamada reaction</a></li> <li><a href="/wiki/Allan%E2%80%93Robinson_reaction" title="Allan–Robinson reaction">Allan–Robinson reaction</a></li> <li><a href="/wiki/Auwers_synthesis" title="Auwers synthesis">Auwers synthesis</a></li> <li><a href="/wiki/Bamberger_triazine_synthesis" title="Bamberger triazine synthesis">Bamberger triazine synthesis</a></li> <li><a href="/wiki/Banert_cascade" title="Banert cascade">Banert cascade</a></li> <li><a href="/wiki/Barton%E2%80%93Zard_reaction" title="Barton–Zard reaction">Barton–Zard reaction</a></li> <li><a href="/wiki/Bernthsen_acridine_synthesis" title="Bernthsen acridine synthesis">Bernthsen acridine synthesis</a></li> <li><a href="/wiki/Bischler%E2%80%93Napieralski_reaction" title="Bischler–Napieralski reaction">Bischler–Napieralski reaction</a></li> <li><a href="/wiki/Bobbitt_reaction" title="Bobbitt reaction">Bobbitt reaction</a></li> <li><a href="/wiki/Boger_pyridine_synthesis" title="Boger pyridine synthesis">Boger pyridine synthesis</a></li> <li><a href="/wiki/Borsche%E2%80%93Drechsel_cyclization" title="Borsche–Drechsel cyclization">Borsche–Drechsel cyclization</a></li> <li><a href="/wiki/Bucherer_carbazole_synthesis" title="Bucherer carbazole synthesis">Bucherer carbazole synthesis</a></li> <li><a href="/wiki/Bucherer%E2%80%93Bergs_reaction" title="Bucherer–Bergs reaction">Bucherer–Bergs reaction</a></li> <li><a href="/wiki/Chichibabin_pyridine_synthesis" title="Chichibabin pyridine synthesis">Chichibabin pyridine synthesis</a></li> <li><a href="/wiki/Cook%E2%80%93Heilbron_thiazole_synthesis" title="Cook–Heilbron thiazole synthesis">Cook–Heilbron thiazole synthesis</a></li> <li><a href="/wiki/Diazoalkane_1,3-dipolar_cycloaddition" title="Diazoalkane 1,3-dipolar cycloaddition">Diazoalkane 1,3-dipolar cycloaddition</a></li> <li><a href="/wiki/Einhorn%E2%80%93Brunner_reaction" title="Einhorn–Brunner reaction">Einhorn–Brunner reaction</a></li> <li><a href="/wiki/Erlenmeyer%E2%80%93Pl%C3%B6chl_azlactone_and_amino-acid_synthesis" title="Erlenmeyer–Plöchl azlactone and amino-acid synthesis">Erlenmeyer–Plöchl azlactone and amino-acid synthesis</a></li> <li><a href="/wiki/Feist%E2%80%93Benary_synthesis" title="Feist–Benary synthesis">Feist–Benary synthesis</a></li> <li><a href="/wiki/Fischer_oxazole_synthesis" title="Fischer oxazole synthesis">Fischer oxazole synthesis</a></li> <li><a href="/wiki/Gabriel%E2%80%93Colman_rearrangement" title="Gabriel–Colman rearrangement">Gabriel–Colman rearrangement</a></li> <li><a href="/wiki/Gewald_reaction" title="Gewald reaction">Gewald reaction</a></li> <li><a href="/wiki/Hantzsch_ester" title="Hantzsch ester">Hantzsch ester</a></li> <li><a href="/wiki/Hantzsch_pyridine_synthesis" title="Hantzsch pyridine synthesis">Hantzsch pyridine synthesis</a></li> <li><a href="/wiki/Herz_reaction" title="Herz reaction">Herz reaction</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Kr%C3%B6hnke_pyridine_synthesis" title="Kröhnke pyridine synthesis">Kröhnke pyridine synthesis</a></li> <li><a href="/w/index.php?title=Lectka_enantioselective_beta-lactam_synthesis&action=edit&redlink=1" class="new" title="Lectka enantioselective beta-lactam synthesis (page does not exist)">Lectka enantioselective beta-lactam synthesis</a></li> <li><a href="/wiki/Lehmstedt%E2%80%93Tanasescu_reaction" title="Lehmstedt–Tanasescu reaction">Lehmstedt–Tanasescu reaction</a></li> <li><a href="/wiki/Niementowski_quinazoline_synthesis" title="Niementowski quinazoline synthesis">Niementowski quinazoline synthesis</a></li> <li><a href="/wiki/Nitrone-olefin_(3%2B2)_cycloaddition" title="Nitrone-olefin (3+2) cycloaddition">Nitrone-olefin (3+2) cycloaddition</a></li> <li><a href="/wiki/Paal%E2%80%93Knorr_synthesis" title="Paal–Knorr synthesis">Paal–Knorr synthesis</a></li> <li><a href="/wiki/Pellizzari_reaction" title="Pellizzari reaction">Pellizzari reaction</a></li> <li><a href="/wiki/Pictet%E2%80%93Spengler_reaction" title="Pictet–Spengler reaction">Pictet–Spengler reaction</a></li> <li><a href="/wiki/Pomeranz%E2%80%93Fritsch_reaction" title="Pomeranz–Fritsch reaction">Pomeranz–Fritsch reaction</a></li> <li><a href="/wiki/Prilezhaev_reaction" title="Prilezhaev reaction">Prilezhaev reaction</a></li> <li><a href="/wiki/Robinson%E2%80%93Gabriel_synthesis" title="Robinson–Gabriel synthesis">Robinson–Gabriel synthesis</a></li> <li><a href="/wiki/Stoll%C3%A9_synthesis" title="Stollé synthesis">Stollé synthesis</a></li> <li><a href="/wiki/Urech_hydantoin_synthesis" title="Urech hydantoin synthesis">Urech hydantoin synthesis</a></li> <li><a href="/wiki/Wenker_synthesis" title="Wenker synthesis">Wenker synthesis</a></li> <li><a href="/wiki/Wohl%E2%80%93Aue_reaction" title="Wohl–Aue reaction">Wohl–Aue reaction</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr></tbody></table><div> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox708" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a 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