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class="vector-toc-numb">2</span> <span>Synthesis of dienes</span> </div> </a> <ul id="toc-Synthesis_of_dienes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactivity_and_uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactivity_and_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reactivity and uses</span> </div> </a> <button aria-controls="toc-Reactivity_and_uses-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 Reactivity and uses subsection</span> </button> <ul id="toc-Reactivity_and_uses-sublist" class="vector-toc-list"> <li id="toc-Polymerization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polymerization"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Polymerization</span> </div> </a> <ul id="toc-Polymerization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cycloadditions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cycloadditions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Cycloadditions</span> </div> </a> <ul id="toc-Cycloadditions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_addition_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_addition_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Other addition reactions</span> </div> </a> <ul id="toc-Other_addition_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metathesis_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metathesis_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Metathesis reactions</span> </div> </a> <ul id="toc-Metathesis_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acidity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acidity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Acidity</span> </div> </a> <ul id="toc-Acidity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-As_ligands" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#As_ligands"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.6</span> <span>As ligands</span> </div> </a> <ul id="toc-As_ligands-sublist" class="vector-toc-list"> </ul> </li> </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">4</span> <span>References</span> </div> </a> <ul id="toc-References-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">Diene</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 43 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-43" 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">43 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/%D8%AF%D9%8A%D9%8A%D9%86" title="ديين – Arabic" lang="ar" hreflang="ar" data-title="ديين" 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/Dienl%C9%99r" title="Dienlər – Azerbaijani" lang="az" hreflang="az" data-title="Dienlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B0%D0%B4%D1%8B%D0%B5%D0%BD%D1%8B" title="Алкадыены – Belarusian" lang="be" hreflang="be" data-title="Алкадыены" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%90%D0%BB%D1%8C%D0%BA%D0%B0%D0%B4%D1%8B%D0%B5%D0%BD%D1%8B" title="Алькадыены – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Алькадыены" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B0%D0%B4%D0%B8%D0%B5%D0%BD%D0%B8" title="Алкадиени – Bulgarian" lang="bg" hreflang="bg" data-title="Алкадиени" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Di%C3%A8" title="Diè – Catalan" lang="ca" hreflang="ca" data-title="Diè" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs badge-Q70893996 mw-list-item" title=""><a href="https://cs.wikipedia.org/wiki/Alkadieny" title="Alkadieny – Czech" lang="cs" hreflang="cs" data-title="Alkadieny" 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/Diene" title="Diene – German" lang="de" hreflang="de" data-title="Diene" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Dieenid" title="Dieenid – Estonian" lang="et" hreflang="et" data-title="Dieenid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BB%CE%BA%CE%B1%CE%B4%CE%B9%CE%AD%CE%BD%CE%B9%CE%B1" title="Αλκαδιένια – Greek" lang="el" hreflang="el" data-title="Αλκαδιένια" 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/Dieno" title="Dieno – Spanish" lang="es" hreflang="es" data-title="Dieno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Dieno" title="Dieno – Basque" lang="eu" hreflang="eu" data-title="Dieno" 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/%D8%AF%DB%8C%E2%80%8C%D8%A7%D9%86" title="دی‌ان – Persian" lang="fa" hreflang="fa" data-title="دی‌ان" 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/Di%C3%A8ne" title="Diène – French" lang="fr" hreflang="fr" data-title="Diène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%8B%A4%EC%9D%B4%EC%97%94" title="다이엔 – Korean" lang="ko" hreflang="ko" data-title="다이엔" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B4%D5%AB%D5%A5%D5%B6%D5%B6%D5%A5%D6%80" title="Դիեններ – Armenian" lang="hy" hreflang="hy" data-title="Դիեններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Diena" title="Diena – Indonesian" lang="id" hreflang="id" data-title="Diena" 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/Dieni" title="Dieni – Italian" lang="it" hreflang="it" data-title="Dieni" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%90%E1%83%9A%E1%83%99%E1%83%90%E1%83%93%E1%83%98%E1%83%94%E1%83%9C%E1%83%94%E1%83%91%E1%83%98" title="ალკადიენები – Georgian" lang="ka" hreflang="ka" data-title="ალკადიენები" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B0%D0%B4%D0%B8%D0%B5%D0%BD%D0%B4%D0%B5%D1%80" title="Алкадиендер – Kazakh" lang="kk" hreflang="kk" data-title="Алкадиендер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%94%D0%B8%D0%B5%D0%BD_%D1%83%D0%B3%D0%BB%D0%B5%D0%B2%D0%BE%D0%B4%D0%BE%D1%80%D0%BE%D0%B4%D0%B4%D0%BE%D1%80%D1%83" title="Диен углеводороддору – Kyrgyz" lang="ky" hreflang="ky" data-title="Диен углеводороддору" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Alkadi%C4%93ni" title="Alkadiēni – Latvian" lang="lv" hreflang="lv" data-title="Alkadiēni" 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/Di%C3%A9n" title="Dién – Hungarian" lang="hu" hreflang="hu" data-title="Dién" 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%94%D0%B8%D0%B5%D0%BD" title="Диен – Macedonian" lang="mk" hreflang="mk" data-title="Диен" 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/Alkadieen" title="Alkadieen – Dutch" lang="nl" hreflang="nl" data-title="Alkadieen" 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%82%B8%E3%82%A8%E3%83%B3" title="ジエン – Japanese" lang="ja" hreflang="ja" data-title="ジエン" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Alkadiyenlar" title="Alkadiyenlar – Uzbek" lang="uz" hreflang="uz" data-title="Alkadiyenlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Dieny" title="Dieny – Polish" lang="pl" hreflang="pl" data-title="Dieny" 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/Alcadieno" title="Alcadieno – Portuguese" lang="pt" hreflang="pt" data-title="Alcadieno" 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/Alcadien%C4%83" title="Alcadienă – Romanian" lang="ro" hreflang="ro" data-title="Alcadienă" 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%94%D0%B8%D0%B5%D0%BD%D1%8B" title="Диены – Russian" lang="ru" hreflang="ru" data-title="Диены" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Diene" title="Diene – Simple English" lang="en-simple" hreflang="en-simple" data-title="Diene" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Di%C3%A9n" title="Dién – Slovak" lang="sk" hreflang="sk" data-title="Dién" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%94%D0%B8%D0%B5%D0%BD" title="Диен – Serbian" lang="sr" hreflang="sr" data-title="Диен" 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/Dien" title="Dien – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Dien" 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/Dieenit" title="Dieenit – Finnish" lang="fi" hreflang="fi" data-title="Dieenit" 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/Dien" title="Dien – Swedish" lang="sv" hreflang="sv" data-title="Dien" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%86%E0%AE%B2%E0%AF%8D%E0%AE%95%E0%AE%BE%E0%AE%9F%E0%AF%88%E0%AE%AF%E0%AF%80%E0%AE%A9%E0%AF%8D" title="ஆல்காடையீன் – Tamil" lang="ta" hreflang="ta" data-title="ஆல்காடையீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/Diennar" title="Diennar – Tatar" lang="tt" hreflang="tt" data-title="Diennar" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Dien" title="Dien – Turkish" lang="tr" hreflang="tr" data-title="Dien" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%94%D1%96%D1%94%D0%BD%D0%B8" title="Дієни – Ukrainian" lang="uk" hreflang="uk" data-title="Дієни" 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/Alkadien" title="Alkadien – Vietnamese" lang="vi" hreflang="vi" data-title="Alkadien" 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-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%BA%8C%E7%83%AF%E7%83%83" title="二烯烃 – Chinese" lang="zh" hreflang="zh" data-title="二烯烃" 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/Q192678#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/Diene" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Diene" rel="discussion" title="Discuss 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<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">Covalent compound that contains two double bonds</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">This article is about organic chemicals. For the surname "Diene" used in West Africa, see <a href="/wiki/Serer_people" title="Serer people">Serer people</a>.</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:1,3-butadiene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/1%2C3-butadiene.svg/150px-1%2C3-butadiene.svg.png" decoding="async" width="150" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/1%2C3-butadiene.svg/225px-1%2C3-butadiene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/43/1%2C3-butadiene.svg/300px-1%2C3-butadiene.svg.png 2x" data-file-width="1024" data-file-height="800" /></a><figcaption><a href="/wiki/1,3-Butadiene" class="mw-redirect" title="1,3-Butadiene">1,3-butadiene</a></figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>diene</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="'d' in 'dye'">d</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key"><i title="English pronunciation respelling"><span style="font-size:90%">DY</span>-een</i></a>); also <b>diolefin</b>, <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="'d' in 'dye'">d</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="'l' in 'lie'">l</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'f' in 'find'">f</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key"><i title="English pronunciation respelling">dy-<span style="font-size:90%">OH</span>-lə-fin</i></a>) or <b>alkadiene</b>) is a <a href="/wiki/Covalent_compound" class="mw-redirect" title="Covalent compound">covalent compound</a> that contains two <a href="/wiki/Double_bond" title="Double bond">double bonds</a>, usually among <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms.<sup id="cite_ref-IUPAC_dienes_1-0" class="reference"><a href="#cite_note-IUPAC_dienes-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They thus contain two <a href="/wiki/Alkene" title="Alkene">alk<i>ene</i></a> units, with the standard prefix <i>di</i> of <a href="/wiki/Systematic_nomenclature" class="mw-redirect" title="Systematic nomenclature">systematic nomenclature</a>. As a subunit of more complex molecules, dienes occur in naturally occurring and synthetic chemicals and are used in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>. <a href="/wiki/Conjugated_system" title="Conjugated system">Conjugated</a> dienes are widely used as <a href="/wiki/Monomer" title="Monomer">monomers</a> in the <a href="/wiki/Polymer" title="Polymer">polymer</a> industry. <a href="/wiki/Polyunsaturated_fat" title="Polyunsaturated fat">Polyunsaturated fats</a> are of interest to <a href="/wiki/Nutrition" title="Nutrition">nutrition</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Classes">Classes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Diene&action=edit&section=1" title="Edit section: Classes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Dienes can be divided into three classes, depending on the relative location of the double bonds:<sup id="cite_ref-IUPAC_dienes_1-1" class="reference"><a href="#cite_note-IUPAC_dienes-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <ol><li><b>Cumulated dienes</b> have the double bonds sharing a common atom. The result is more specifically called an <a href="/wiki/Allene" class="mw-redirect" title="Allene">allene</a>.</li> <li><b>Conjugated dienes</b> have <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated</a> double bonds separated by one single bond. Conjugated dienes are more stable than other dienes because of resonance.</li> <li><b>Unconjugated dienes</b> have the double bonds separated by two or more single bonds. They are usually less stable than <a href="/wiki/Isomer" title="Isomer">isomeric</a> conjugated dienes. This can also be known as an <b>isolated</b> diene.</li></ol> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Dienes_various_examples.png" class="mw-file-description"><img alt="Structure of various alkadienes (also called dienes or diolefins)" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Dienes_various_examples.png/960px-Dienes_various_examples.png" decoding="async" width="650" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Dienes_various_examples.png/975px-Dienes_various_examples.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Dienes_various_examples.png/1300px-Dienes_various_examples.png 2x" data-file-width="2341" data-file-height="441" /></a><figcaption>Some dienes: <b>A</b>: 1,2-Propadiene, also known as <a href="/wiki/Allene" class="mw-redirect" title="Allene">allene</a>, is the simplest cumulated diene. <b>B</b>: <a href="/wiki/Isoprene" title="Isoprene">Isoprene</a>, also known as 2-methyl-1,3-butadiene, the precursor to natural rubber. <b>C</b>: <a href="/wiki/1,3-Butadiene" class="mw-redirect" title="1,3-Butadiene">1,3-Butadiene</a>, a precursor to synthetic polymers. <b>D</b>: <a href="/wiki/1,5-Cyclooctadiene" title="1,5-Cyclooctadiene">1,5-Cyclooctadiene</a>, an unconjugated diene (notice that each double bond is two carbons away from the other). <b>E</b>: <a href="/wiki/Norbornadiene" title="Norbornadiene">Norbornadiene</a>, a strained bicyclic and unconjugated diene. <b>F</b>: <a href="/wiki/Dicyclopentadiene" title="Dicyclopentadiene">Dicyclopentadiene</a>.</figcaption></figure> <p>According to the <i><a href="/wiki/Gold_Book" class="mw-redirect" title="Gold Book">Gold Book</a></i> definition, a "diene" could include one or more <a href="/wiki/Heteroatom" title="Heteroatom">heteroatoms</a> which replace unsaturated carbon atoms, giving structures that could more specifically be called <i>heterodienes</i>.<sup id="cite_ref-IUPAC_dienes_1-2" class="reference"><a href="#cite_note-IUPAC_dienes-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Compounds that contain more than two double bonds are called <a href="/wiki/Polyene" title="Polyene">polyenes</a>. Polyenes and dienes share many properties. </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis_of_dienes">Synthesis of dienes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Diene&action=edit&section=2" title="Edit section: Synthesis of dienes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>On an industrial scale, butadiene is prepared by <a href="/wiki/Thermal_cracking" class="mw-redirect" title="Thermal cracking">thermal cracking</a> of <a href="/wiki/Butane" title="Butane">butanes</a>. In a similarly non-selective process, <a href="/wiki/Dicyclopentadiene" title="Dicyclopentadiene">dicyclopentadiene</a> is obtained from <a href="/wiki/Coal_tar" title="Coal tar">coal tars</a>. </p><p>In the laboratory, more directed and more delicate processes are employed such as <a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">dehydrohalogenations</a> and <a href="/wiki/Condensation_(chemistry)" class="mw-redirect" title="Condensation (chemistry)">condensations</a>. Myriad <a href="/wiki/Organic_reaction" title="Organic reaction">methods</a> have been developed, such as the <a href="/wiki/Whiting_reaction" title="Whiting reaction">Whiting reaction</a>. Families of nonconjugated dienes are derived from the <a href="/wiki/Oligomerization" class="mw-redirect" title="Oligomerization">oligomerization</a> and <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimerization</a> of conjugated dienes. For example, 1,5-cyclooctadiene and 4-vinylcyclohexene are produced by dimerization of <a href="/wiki/1,3-Butadiene" class="mw-redirect" title="1,3-Butadiene">1,3-butadiene</a>. </p><p>Diene-containing <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a> are <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesized</a> from <a href="/wiki/Acetyl_CoA" class="mw-redirect" title="Acetyl CoA">acetyl CoA</a>. </p><p>α,ω-Dienes have the formula (CH<sub>2</sub>)<sub>n</sub>(CH=CH<sub>2</sub>)<sub>2</sub>. They are prepared industrially by <a href="/wiki/Ethenolysis" title="Ethenolysis">ethenolysis</a> of cyclic dienes. For example, <a href="/wiki/1,5-Hexadiene" title="1,5-Hexadiene">1,5-hexadiene</a> and 1,9-decadiene, useful crosslinking agents and synthetic intermediates, are produced from <a href="/wiki/1,5-Cyclooctadiene" title="1,5-Cyclooctadiene">1,5-cyclooctadiene</a> and <a href="/wiki/Cyclooctene" title="Cyclooctene">cyclooctene</a>, respectively. The catalyst is derived from Re<sub>2</sub>O<sub>7</sub> on alumina.<sup id="cite_ref-KO_2-0" class="reference"><a href="#cite_note-KO-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactivity_and_uses">Reactivity and uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Diene&action=edit&section=3" title="Edit section: Reactivity and uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Polymerization">Polymerization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Diene&action=edit&section=4" title="Edit section: Polymerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The most heavily practiced reaction of alkenes, dienes included, is <a href="/wiki/Polymerization" title="Polymerization">polymerization</a>. 1,3-Butadiene is a precursor to <a href="/wiki/Synthetic_rubber" title="Synthetic rubber">rubber</a> used in tires, and <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> is the precursor to <a href="/wiki/Natural_rubber" title="Natural rubber">natural rubber</a>. <a href="/wiki/Chloroprene" title="Chloroprene">Chloroprene</a> is related but it is a synthetic monomer. </p> <div class="mw-heading mw-heading3"><h3 id="Cycloadditions">Cycloadditions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Diene&action=edit&section=5" title="Edit section: Cycloadditions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An important reaction for conjugated dienes is the <a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a>. Many specialized dienes have been developed to exploit this reactivity for the synthesis of <a href="/wiki/Natural_product" title="Natural product">natural products</a> (e.g., <a href="/wiki/Danishefsky%27s_diene" title="Danishefsky's diene">Danishefsky's diene</a>). </p> <div class="mw-heading mw-heading3"><h3 id="Other_addition_reactions">Other addition reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Diene&action=edit&section=6" title="Edit section: Other addition reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Conjugated dienes add reagents such as <a href="/wiki/Bromine" title="Bromine">bromine</a> and <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> by both 1,2-addition and 1,4-addition pathways. Addition of polar reagents can generate complex architectures:<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><dl><dd><span typeof="mw:File"><a href="/wiki/File:CODSCl2.png" class="mw-file-description" title="2,6-Dichloro-9-thiabicyclo[3.3.1]nonane, synthesis and reactions"><img alt="2,6-Dichloro-9-thiabicyclo[3.3.1]nonane, synthesis and reactions" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/CODSCl2.png/500px-CODSCl2.png" decoding="async" width="450" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/CODSCl2.png/960px-CODSCl2.png 1.5x" data-file-width="1296" data-file-height="246" /></a></span></dd></dl></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Metathesis_reactions">Metathesis reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Diene&action=edit&section=7" title="Edit section: Metathesis reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nonconjugated dienes are substrates for <a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">ring-closing metathesis</a> reactions. These reactions require a metal <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>:c </p> <dl><dd><dl><dd><span typeof="mw:File"><a href="/wiki/File:RCM_cyclophane_example.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/RCM_cyclophane_example.png/520px-RCM_cyclophane_example.png" decoding="async" width="520" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/RCM_cyclophane_example.png/780px-RCM_cyclophane_example.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f0/RCM_cyclophane_example.png/1040px-RCM_cyclophane_example.png 2x" data-file-width="1049" data-file-height="302" /></a></span></dd></dl></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Acidity">Acidity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Diene&action=edit&section=8" title="Edit section: Acidity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The position adjacent to a double bond is <a href="/wiki/Acid" title="Acid">acidic</a> because the resulting <a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allyl</a> anion is stabilized by resonance. This effect becomes more pronounced as more alkenes are involved to create greater stability. For example, deprotonation at position 3 of a 1,4-diene or position 5 of a 1,3-diene give a <a href="/wiki/Pentadienyl" class="mw-redirect" title="Pentadienyl">pentadienyl</a> anion. An even greater effect is seen if the anion is aromatic, for example, deprotonation of <a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a> to give the <a href="/wiki/Cyclopentadienyl_anion" title="Cyclopentadienyl anion">cyclopentadienyl anion</a>. </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:HayashiChiralNBD.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/HayashiChiralNBD.svg/122px-HayashiChiralNBD.svg.png" decoding="async" width="122" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/HayashiChiralNBD.svg/183px-HayashiChiralNBD.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/HayashiChiralNBD.svg/244px-HayashiChiralNBD.svg.png 2x" data-file-width="1304" data-file-height="826" /></a><figcaption><a href="/wiki/C2-Symmetric_ligands" title="C2-Symmetric ligands">C<sub>2</sub>-symmetric</a> diene ligand used in <a href="/wiki/Asymmetric_catalysis" class="mw-redirect" title="Asymmetric catalysis">asymmetric catalysis</a>.<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></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="As_ligands">As ligands</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Diene&action=edit&section=9" title="Edit section: As ligands"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Dienes are widely used chelating <a href="/wiki/Ligand" title="Ligand">ligands</a> in <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>. In some cases they serve as placeholder ligands, being removed during a catalytic cycle. For example, the cyclooctadiene ("cod") ligands in <a href="/wiki/Bis(cyclooctadiene)nickel(0)" title="Bis(cyclooctadiene)nickel(0)">bis(cyclooctadiene)nickel(0)</a> are labile. In some cases, dienes are spectator ligands, remaining coordinated throughout a catalytic cycle and influencing the product distributions. <a href="/wiki/Chirality" title="Chirality">Chiral</a> dienes have also been described.<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> Other diene complexes include <a href="/wiki/(Butadiene)iron_tricarbonyl" title="(Butadiene)iron tricarbonyl">(butadiene)iron tricarbonyl</a>, <a href="/wiki/Cyclobutadieneiron_tricarbonyl" title="Cyclobutadieneiron tricarbonyl">cyclobutadieneiron tricarbonyl</a>, and <a href="/wiki/Cyclooctadiene_rhodium_chloride_dimer" title="Cyclooctadiene rhodium chloride dimer">cyclooctadiene rhodium chloride dimer</a>. </p> <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=Diene&action=edit&section=10" 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"><ol class="references"> <li id="cite_note-IUPAC_dienes-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-IUPAC_dienes_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IUPAC_dienes_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-IUPAC_dienes_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. 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Noels (2005). "Metathesis". <i>Kirk-Othmer Encyclopedia of Chemical Technology</i>. 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href="/wiki/Template:Hydrocarbons" title="Template:Hydrocarbons"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrocarbons" title="Template talk:Hydrocarbons"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrocarbons" title="Special:EditPage/Template:Hydrocarbons"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hydrocarbons181" style="font-size:114%;margin:0 4em"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a></div></th></tr><tr><th scope="row" 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 class="mw-selflink selflink">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 href="/wiki/Phenanthrene" title="Phenanthrene">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" 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class="vector-sticky-header-end" aria-hidden="true"> <div class="vector-sticky-header-icons"> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-talk-sticky-header" tabindex="-1" data-event-name="talk-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbles mw-ui-icon-wikimedia-speechBubbles"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-subject-sticky-header" tabindex="-1" data-event-name="subject-sticky-header"><span class="vector-icon mw-ui-icon-article mw-ui-icon-wikimedia-article"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-history-sticky-header" tabindex="-1" data-event-name="history-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-history mw-ui-icon-wikimedia-wikimedia-history"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only mw-watchlink" id="ca-watchstar-sticky-header" tabindex="-1" data-event-name="watch-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-star mw-ui-icon-wikimedia-wikimedia-star"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-edit-sticky-header" tabindex="-1" data-event-name="wikitext-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-wikiText mw-ui-icon-wikimedia-wikimedia-wikiText"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-ve-edit-sticky-header" tabindex="-1" data-event-name="ve-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-edit mw-ui-icon-wikimedia-wikimedia-edit"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-viewsource-sticky-header" tabindex="-1" data-event-name="ve-edit-protected-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-editLock mw-ui-icon-wikimedia-wikimedia-editLock"></span> <span></span> </a> </div> <div class="vector-sticky-header-buttons"> <button class="cdx-button cdx-button--weight-quiet mw-interlanguage-selector" id="p-lang-btn-sticky-header" tabindex="-1" data-event-name="ui.dropdown-p-lang-btn-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-language mw-ui-icon-wikimedia-wikimedia-language"></span> <span>43 languages</span> </button> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive" id="ca-addsection-sticky-header" tabindex="-1" data-event-name="addsection-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbleAdd-progressive mw-ui-icon-wikimedia-speechBubbleAdd-progressive"></span> <span>Add topic</span> </a> </div> <div class="vector-sticky-header-icon-end"> <div class="vector-user-links"> </div> </div> </div> </div> </div> <div class="mw-portlet mw-portlet-dock-bottom emptyPortlet" id="p-dock-bottom"> <ul> </ul> </div> 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