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<span>Nomenclature</span> </div> </a> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Properties</span> </div> </a> <ul id="toc-Properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Trans_isomers" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Trans_isomers"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Trans isomers</span> </div> </a> <ul id="toc-Trans_isomers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis_reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Synthesis reactions</span> </div> </a> <button aria-controls="toc-Synthesis_reactions-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 Synthesis reactions subsection</span> </button> <ul id="toc-Synthesis_reactions-sublist" class="vector-toc-list"> <li id="toc-Ring-closing_metathesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ring-closing_metathesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Ring-closing metathesis</span> </div> </a> <ul id="toc-Ring-closing_metathesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Birch_reduction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Birch_reduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Birch reduction</span> </div> </a> <ul id="toc-Birch_reduction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Diels-Alder_reaction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Diels-Alder_reaction"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Diels-Alder reaction</span> </div> </a> <ul id="toc-Diels-Alder_reaction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyclization_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cyclization_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Cyclization reactions</span> </div> </a> <ul id="toc-Cyclization_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Electrocyclic_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Electrocyclic_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Electrocyclic reactions</span> </div> </a> <ul id="toc-Electrocyclic_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intramolecular_McMurry_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Intramolecular_McMurry_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.6</span> <span>Intramolecular McMurry reactions</span> </div> </a> <ul id="toc-Intramolecular_McMurry_reactions-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> </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 " 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href="https://be-tarask.wikipedia.org/wiki/%D0%A6%D1%8B%D0%BA%D0%BB%D1%8F%D0%B0%D0%BB%D1%8C%D0%BA%D0%B5%D0%BD%D1%8B" title="Цыкляалькены – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Цыкляалькены" 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-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Cikloalkeni" title="Cikloalkeni – Bosnian" lang="bs" hreflang="bs" data-title="Cikloalkeni" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cicloalqu%C3%A8" title="Cicloalquè – Catalan" lang="ca" hreflang="ca" data-title="Cicloalquè" 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/Cykloalkeny" title="Cykloalkeny – Czech" lang="cs" hreflang="cs" data-title="Cykloalkeny" 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/Cycloalkene" title="Cycloalkene – German" lang="de" hreflang="de" data-title="Cycloalkene" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Cicloalqueno" title="Cicloalqueno – Spanish" lang="es" hreflang="es" data-title="Cicloalqueno" 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/Zikloalkeno" title="Zikloalkeno – Basque" lang="eu" hreflang="eu" data-title="Zikloalkeno" 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%B3%DB%8C%DA%A9%D9%84%D9%88%D8%A2%D9%84%DA%A9%D9%86" title="سیکلوآلکن – Persian" lang="fa" hreflang="fa" data-title="سیکلوآلکن" 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/Cycloalc%C3%A8ne" title="Cycloalcène – French" lang="fr" hreflang="fr" data-title="Cycloalcène" 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/%EC%82%AC%EC%9D%B4%ED%81%B4%EB%A1%9C%EC%95%8C%EC%BC%84" title="사이클로알켄 – Korean" lang="ko" hreflang="ko" data-title="사이클로알켄" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Cikloalkeni" title="Cikloalkeni – Croatian" lang="hr" hreflang="hr" data-title="Cikloalkeni" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Cicloalcheni" title="Cicloalcheni – Italian" lang="it" hreflang="it" data-title="Cicloalcheni" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Cikloalk%C3%A9nek" title="Cikloalkének – Hungarian" lang="hu" hreflang="hu" data-title="Cikloalkének" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AB%E0%B4%B2%E0%B4%95%E0%B4%82:Cycloalkenes" title="ഫലകം:Cycloalkenes – Malayalam" lang="ml" hreflang="ml" data-title="ഫലകം:Cycloalkenes" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Sikloalkena" title="Sikloalkena – Malay" lang="ms" hreflang="ms" data-title="Sikloalkena" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cycloalkeen" title="Cycloalkeen – Dutch" lang="nl" hreflang="nl" data-title="Cycloalkeen" 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%B7%E3%82%AF%E3%83%AD%E3%82%A2%E3%83%AB%E3%82%B1%E3%83%B3" title="シクロアルケン – Japanese" lang="ja" hreflang="ja" data-title="シクロアルケン" 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/Cykloalkeny" title="Cykloalkeny – Polish" lang="pl" hreflang="pl" data-title="Cykloalkeny" 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/Cicloalceno" title="Cicloalceno – Portuguese" lang="pt" hreflang="pt" data-title="Cicloalceno" 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/Cicloalchen%C4%83" title="Cicloalchenă – Romanian" lang="ro" hreflang="ro" data-title="Cicloalchenă" 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%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B5%D0%BD%D1%8B" title="Циклоалкены – Russian" lang="ru" hreflang="ru" data-title="Циклоалкены" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Cykloalk%C3%A9n" title="Cykloalkén – Slovak" lang="sk" hreflang="sk" data-title="Cykloalkén" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Cikloalken" title="Cikloalken – Slovenian" lang="sl" hreflang="sl" data-title="Cikloalken" 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/Cikloalken" title="Cikloalken – Serbian" lang="sr" hreflang="sr" data-title="Cikloalken" 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/Cikloalkeni" title="Cikloalkeni – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cikloalkeni" 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/Sykloalkeenit" title="Sykloalkeenit – Finnish" lang="fi" hreflang="fi" data-title="Sykloalkeenit" 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/Cykloalken" title="Cykloalken – Swedish" lang="sv" hreflang="sv" data-title="Cykloalken" 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%B5%E0%AE%B3%E0%AF%88%E0%AE%AF_%E0%AE%86%E0%AE%B2%E0%AF%8D%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AF%80%E0%AE%A9%E0%AF%8D" title="வளைய ஆல்க்கீன் – Tamil" lang="ta" hreflang="ta" data-title="வளைய ஆல்க்கீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Sikloalken" title="Sikloalken – Turkish" lang="tr" hreflang="tr" data-title="Sikloalken" 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%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B5%D0%BD%D0%B8" title="Циклоалкени – Ukrainian" lang="uk" hreflang="uk" data-title="Циклоалкени" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%8E%AF%E7%83%AF%E7%83%83" title="环烯烃 – Chinese" lang="zh" hreflang="zh" data-title="环烯烃" 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/Q413343#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div 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.ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-More_citations_needed plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Cycloalkene" title="Special:EditPage/Cycloalkene">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a>. Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Cycloalkene%22">"Cycloalkene"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Cycloalkene%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Cycloalkene%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Cycloalkene%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Cycloalkene%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Cycloalkene%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">December 2009</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>cycloalkene</b> or <b>cycloolefin</b> is a type of <a href="/wiki/Alkene" title="Alkene">alkene</a> <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> which contains a closed <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a> of <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms and either one or more <a href="/wiki/Double_bond" title="Double bond">double bonds</a>, but has no <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a> character. Some cycloalkenes, such as <a href="/wiki/Cyclobutene" title="Cyclobutene">cyclobutene</a> and <a href="/wiki/Cyclopentene" title="Cyclopentene">cyclopentene</a>, can be used as <a href="/wiki/Monomer" title="Monomer">monomers</a> to produce <a href="/wiki/Polymer" title="Polymer">polymer</a> chains.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Due to geometrical considerations, smaller cycloalkenes are almost always the <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism"><i>cis</i> isomers</a>, and the term <i>cis</i> tends to be omitted from the names. Cycloalkenes require considerable <a href="/wiki/P-orbital" class="mw-redirect" title="P-orbital">p-orbital</a> overlap in the form of a bridge between the carbon-carbon double bond; however, this is not feasible in smaller molecules due to the increase of <a href="/wiki/Ring_strain" title="Ring strain">strain</a> that could break the molecule apart. In greater carbon number cycloalkenes, the addition of <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub></span> <a href="/wiki/Substituent" title="Substituent">substituents</a> decreases strain.<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> trans-Cycloalkenes with 7 or fewer carbons in the ring will not occur under normal conditions because of the large amount of ring strain needed. In larger rings (8 or more atoms), <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism"><i>cis</i>–<i>trans</i> isomerism</a> of the double bond may occur. This stability pattern forms part of the origin of <a href="/wiki/Bredt%27s_rule" title="Bredt's rule">Bredt's rule</a>, the observation that alkenes do not form at the bridgehead of many types of <a href="/wiki/Bridged_compounds" class="mw-redirect" title="Bridged compounds">bridged</a> ring systems because the alkene would necessarily be <i>trans</i> in one of the rings. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkene&action=edit&section=1" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cyclopropene_2D_skeletal.svg" class="mw-file-description" title="Cyclopropene"><img alt="Cyclopropene" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyclopropene_2D_skeletal.svg/120px-Cyclopropene_2D_skeletal.svg.png" decoding="async" width="120" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyclopropene_2D_skeletal.svg/180px-Cyclopropene_2D_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyclopropene_2D_skeletal.svg/240px-Cyclopropene_2D_skeletal.svg.png 2x" data-file-width="529" data-file-height="471" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cyclobutene.svg" class="mw-file-description" title="Cyclobutene"><img alt="Cyclobutene" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Cyclobutene.svg/120px-Cyclobutene.svg.png" decoding="async" width="120" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Cyclobutene.svg/180px-Cyclobutene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Cyclobutene.svg/240px-Cyclobutene.svg.png 2x" data-file-width="200" data-file-height="200" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cyclopentene.svg" class="mw-file-description" title="Cyclopentene"><img alt="Cyclopentene" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Cyclopentene.svg/114px-Cyclopentene.svg.png" decoding="async" width="114" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Cyclopentene.svg/171px-Cyclopentene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Cyclopentene.svg/228px-Cyclopentene.svg.png 2x" data-file-width="266" data-file-height="280" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cyclohexene.svg" class="mw-file-description" title="Cyclohexene"><img alt="Cyclohexene" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Cyclohexene.svg/104px-Cyclohexene.svg.png" decoding="async" width="104" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Cyclohexene.svg/155px-Cyclohexene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Cyclohexene.svg/207px-Cyclohexene.svg.png 2x" data-file-width="70" data-file-height="81" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cycloheptene.svg" class="mw-file-description" title="Cycloheptene"><img alt="Cycloheptene" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Cycloheptene.svg/120px-Cycloheptene.svg.png" decoding="async" width="120" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Cycloheptene.svg/180px-Cycloheptene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/62/Cycloheptene.svg/240px-Cycloheptene.svg.png 2x" data-file-width="128" data-file-height="128" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:1,3-cyclohexadiene.svg" class="mw-file-description" title="1,3-Cyclohexadiene"><img alt="1,3-Cyclohexadiene" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/1%2C3-cyclohexadiene.svg/110px-1%2C3-cyclohexadiene.svg.png" decoding="async" width="110" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/1%2C3-cyclohexadiene.svg/165px-1%2C3-cyclohexadiene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3c/1%2C3-cyclohexadiene.svg/221px-1%2C3-cyclohexadiene.svg.png 2x" data-file-width="193" data-file-height="210" /></a></span></div> <div class="gallerytext"><a href="/wiki/1,3-Cyclohexadiene" class="mw-redirect" title="1,3-Cyclohexadiene">1,3-Cyclohexadiene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:1,4-cyclohexadiene.svg" class="mw-file-description" title="1,4-Cyclohexadiene"><img alt="1,4-Cyclohexadiene" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/1%2C4-cyclohexadiene.svg/110px-1%2C4-cyclohexadiene.svg.png" decoding="async" width="110" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/54/1%2C4-cyclohexadiene.svg/165px-1%2C4-cyclohexadiene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/54/1%2C4-cyclohexadiene.svg/221px-1%2C4-cyclohexadiene.svg.png 2x" data-file-width="193" data-file-height="210" /></a></span></div> <div class="gallerytext"><a href="/wiki/1,4-Cyclohexadiene" class="mw-redirect" title="1,4-Cyclohexadiene">1,4-Cyclohexadiene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:1,5-Cyclooctadiene.svg" class="mw-file-description" title="1,5-Cyclooctadiene"><img alt="1,5-Cyclooctadiene" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/1%2C5-Cyclooctadiene.svg/111px-1%2C5-Cyclooctadiene.svg.png" decoding="async" width="111" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/1%2C5-Cyclooctadiene.svg/167px-1%2C5-Cyclooctadiene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/1%2C5-Cyclooctadiene.svg/223px-1%2C5-Cyclooctadiene.svg.png 2x" data-file-width="130" data-file-height="140" /></a></span></div> <div class="gallerytext"><a href="/wiki/1,5-Cyclooctadiene" title="1,5-Cyclooctadiene">1,5-Cyclooctadiene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cis-cyclooctene.png" class="mw-file-description" title="cis-cyclooctene"><img alt="cis-cyclooctene" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Cis-cyclooctene.png/120px-Cis-cyclooctene.png" decoding="async" width="120" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Cis-cyclooctene.png/180px-Cis-cyclooctene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Cis-cyclooctene.png/240px-Cis-cyclooctene.png 2x" data-file-width="776" data-file-height="776" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cis-Cyclooctene" title="Cis-Cyclooctene">cis-cyclooctene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:(S)-(%2B)-trans-Cyclooctene_Structural_Formula_V.1.svg" class="mw-file-description" title="trans-cyclooctene"><img alt="trans-cyclooctene" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/%28S%29-%28%2B%29-trans-Cyclooctene_Structural_Formula_V.1.svg/116px-%28S%29-%28%2B%29-trans-Cyclooctene_Structural_Formula_V.1.svg.png" decoding="async" width="116" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/%28S%29-%28%2B%29-trans-Cyclooctene_Structural_Formula_V.1.svg/175px-%28S%29-%28%2B%29-trans-Cyclooctene_Structural_Formula_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/%28S%29-%28%2B%29-trans-Cyclooctene_Structural_Formula_V.1.svg/233px-%28S%29-%28%2B%29-trans-Cyclooctene_Structural_Formula_V.1.svg.png 2x" data-file-width="231" data-file-height="238" /></a></span></div> <div class="gallerytext"><a href="/wiki/Trans-Cyclooctene" title="Trans-Cyclooctene">trans-cyclooctene</a></div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkene&action=edit&section=2" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div><p> Cycloalkenes follow a similar <a href="/wiki/Nomenclature_of_Organic_Chemistry" title="Nomenclature of Organic Chemistry">nomenclature</a> system to <a href="/wiki/Alkene" title="Alkene">alkenes</a>, but the carbons are numbered starting at a carbon on the double bond and then through the double bond and around the ring.<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> This method is used to keep the index numbers small. </p><ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Cycloalkene_nomenclature.svg" class="mw-file-description" title="1-methylcyclohexene"><img alt="1-methylcyclohexene" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Cycloalkene_nomenclature.svg/83px-Cycloalkene_nomenclature.svg.png" decoding="async" width="83" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Cycloalkene_nomenclature.svg/124px-Cycloalkene_nomenclature.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Cycloalkene_nomenclature.svg/166px-Cycloalkene_nomenclature.svg.png 2x" data-file-width="512" data-file-height="741" /></a></span></div> <div class="gallerytext">1-methylcyclohexene</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:3-methylcyclohexene_nomenclature.svg" class="mw-file-description" title="3-methylcyclohexene"><img alt="3-methylcyclohexene" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/3-methylcyclohexene_nomenclature.svg/85px-3-methylcyclohexene_nomenclature.svg.png" decoding="async" width="85" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/3-methylcyclohexene_nomenclature.svg/127px-3-methylcyclohexene_nomenclature.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/3-methylcyclohexene_nomenclature.svg/169px-3-methylcyclohexene_nomenclature.svg.png 2x" data-file-width="512" data-file-height="725" /></a></span></div> <div class="gallerytext">3-methylcyclohexene</div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkene&action=edit&section=3" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cycloalkenes with a small ring have about 20° more bond angle strain than a cycloalkane of the same size.<sup id="cite_ref-:02_4-0" class="reference"><a href="#cite_note-:02-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> This is because the bond angle for an alkene, C-C=C, is 122°, while the bond angle for an alkane, C-C-C, is 112°. When these carbons form a small ring, the alkene which has a larger bond angle will have to compress more than the alkane causing more bond angle strain.<sup id="cite_ref-:02_4-1" class="reference"><a href="#cite_note-:02-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Cycloalkenes have a lower melting point than cycloalkanes of the same size. The lowered melting point is due to the double bond preventing the compound from compact packing. </p><p>Cycloalkenes generally reflect physical properties of their cycloalkane. In physical states, only the smaller cycloalkenes are gases while the others are mostly liquid. These molecules are also more reactive than cycloalkanes due to increased electron density shifts of the double bond. <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> </p> <div class="mw-heading mw-heading2"><h2 id="Trans_isomers">Trans isomers</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkene&action=edit&section=4" title="Edit section: Trans isomers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As previously mentioned, cis-isomers of cycloalkenes exhibit more stability than trans-isomers; however, on an experimental and computational level, this property is only applicable to cycloalkenes with 10 carbons or less. As the number of carbons increase, the possibility of a trans-isomer occurring also increase.<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> The geometrical considerations as analyzed by computational analysis are as follows. </p><p>The most stable trans-isomers of 10 ring or greater cycloalkenes exhibit 4  irregularities from standard geometric norms. The first irregularity is twisted planes of substituents along the C=C. Using C=C as the stable axis, 2 substituents of 1 carbon can be visualized on the same plane, equally applied to the other carbon. These planes are not planar and instead one carbon substituent plane twists along the axis away or toward the other carbon’s plane. This twisting leads to pyramidalization forming a <a href="/wiki/Pyramidal_alkene" title="Pyramidal alkene">pyramidal alkene</a> which is the second irregularity. A greater angle of twisting, usually results in lower carbon number rings and decreases as the carbon number increases. <a href="/wiki/Pyramidalization" class="mw-redirect" title="Pyramidalization">Pyramidalization</a> is important in highered number rings, because it increases p-orbital overlap for stability, and reduces torsional strain. <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> </p><p>Bond length between the C=C and corresponding vinylic carbons also vary. In smaller cycloalkenes, it is expected for the bonds to be greater in length uniformly to account for increased strain, but for example, trans-cycloheptane has varying bond lengths. Also, the vinylic carbons on trans cyclohexanes exhibit longer bond lengths than their respective cis isomer for trans-cycloheptane through trans-cyclononene (7 carbon and 9 carbon cycloalkenes).<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> <div class="mw-heading mw-heading2"><h2 id="Synthesis_reactions">Synthesis reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkene&action=edit&section=5" title="Edit section: Synthesis reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Ring-closing_metathesis">Ring-closing metathesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkene&action=edit&section=6" title="Edit section: Ring-closing metathesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">Ring-closing metathesis</a> switches out functional groups from one or multiple terminal alkenes to form a cycloalkene.<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> This process can be used to form cycloalkenes of either E or Z configurations, depending on the stereochemistry of the second ring strain.<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> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:RingClosingEnyneMetathesis.png" class="mw-file-description" title="Formation of a cycloalkane via ring closing metathesis"><img alt="Formation of a cycloalkane via ring closing metathesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/RingClosingEnyneMetathesis.png/220px-RingClosingEnyneMetathesis.png" decoding="async" width="220" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/RingClosingEnyneMetathesis.png/330px-RingClosingEnyneMetathesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/RingClosingEnyneMetathesis.png/440px-RingClosingEnyneMetathesis.png 2x" data-file-width="675" data-file-height="212" /></a><figcaption>Formation of a cycloalkane via ring closing metathesis</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Birch_reduction">Birch reduction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkene&action=edit&section=7" title="Edit section: Birch reduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Birch_reduction" title="Birch reduction">Birch reduction</a> is a possible method to reduce reduces aromatic compounds into cycloalkenes, specifically cyclohexadiene.<sup id="cite_ref-:0_11-0" class="reference"><a href="#cite_note-:0-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Birch_reduction_benzoate.svg" class="mw-file-description" title="Formation of a cycloalkane via Birch Reduction"><img alt="Formation of a cycloalkane via Birch Reduction" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Birch_reduction_benzoate.svg/220px-Birch_reduction_benzoate.svg.png" decoding="async" width="220" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Birch_reduction_benzoate.svg/330px-Birch_reduction_benzoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Birch_reduction_benzoate.svg/440px-Birch_reduction_benzoate.svg.png 2x" data-file-width="220" data-file-height="81" /></a><figcaption>Formation of a cycloalkane via Birch Reduction</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Diels-Alder_reaction">Diels-Alder reaction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkene&action=edit&section=8" title="Edit section: Diels-Alder reaction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Diels-Alder_reaction" class="mw-redirect" title="Diels-Alder reaction">Diels-Alder reaction</a>, also known as cycloaddition, combines a conjugated diene and an alkene to form cycloalkene. This is a concerted process, with bonds forming and breaking simultaneously.<sup id="cite_ref-:0_11-1" class="reference"><a href="#cite_note-:0-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Diels-Alder_(1,3-butadiene_%2B_ethylene).svg" class="mw-file-description" title="Formation of a cycloalkane via a Diels-Alder Reaction"><img alt="Formation of a cycloalkane via a Diels-Alder Reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/10/Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29.svg/220px-Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29.svg.png" decoding="async" width="220" height="59" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/10/Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29.svg/330px-Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/10/Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29.svg/440px-Diels-Alder_%281%2C3-butadiene_%2B_ethylene%29.svg.png 2x" data-file-width="615" data-file-height="165" /></a><figcaption>Formation of a cycloalkane via a Diels-Alder Reaction</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Cyclization_reactions">Cyclization reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkene&action=edit&section=9" title="Edit section: Cyclization reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Cyclization_reaction" class="mw-redirect" title="Cyclization reaction">Cyclization reactions</a>, or intramolecular addition reactions, can be used to form cycloalkenes. These reactions primarily form cyclopentenones, a cycloalkene that contains two functional groups: the cyclopentene and a ketone group.<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> However, other cycloalkenes, such as Cyclooctatetraene, can be formed as a result of this reaction.<sup id="cite_ref-:0_11-2" class="reference"><a href="#cite_note-:0-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:GPP_cyclization_to_elisabethatriene.tif" class="mw-file-description" title="Formation of a cyclohexane from a non-cyclic compound via a Cyclization Reaction"><img alt="Formation of a cyclohexane from a non-cyclic compound via a Cyclization Reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/GPP_cyclization_to_elisabethatriene.tif/lossless-page1-350px-GPP_cyclization_to_elisabethatriene.tif.png" decoding="async" width="350" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/GPP_cyclization_to_elisabethatriene.tif/lossless-page1-525px-GPP_cyclization_to_elisabethatriene.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/GPP_cyclization_to_elisabethatriene.tif/lossless-page1-700px-GPP_cyclization_to_elisabethatriene.tif.png 2x" data-file-width="1975" data-file-height="816" /></a><figcaption>Formation of a cyclohexane from a non-cyclic compound via a Cyclization Reaction</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Electrocyclic_reactions">Electrocyclic reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkene&action=edit&section=10" title="Edit section: Electrocyclic reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Reactions of conjugated double-bond systems can be synthesized into cycloalkenes through <a href="/wiki/Electrocyclic_reaction" title="Electrocyclic reaction">electrocyclic reactions</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> Addition of heat or photolysis causes a reversible reaction that causes one pi bond to become a sigma bond, which closes the ring and creates a cycloalkene.<sup id="cite_ref-:0_11-3" class="reference"><a href="#cite_note-:0-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Electrocyclic_reaction_-_arrows.svg" class="mw-file-description" title="Formation of a cycloalkane via an electrocyclic reaction"><img alt="Formation of a cycloalkane via an electrocyclic reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Electrocyclic_reaction_-_arrows.svg/220px-Electrocyclic_reaction_-_arrows.svg.png" decoding="async" width="220" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Electrocyclic_reaction_-_arrows.svg/330px-Electrocyclic_reaction_-_arrows.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/87/Electrocyclic_reaction_-_arrows.svg/440px-Electrocyclic_reaction_-_arrows.svg.png 2x" data-file-width="467" data-file-height="165" /></a><figcaption>Formation of a cycloalkane via an electrocyclic reaction</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Intramolecular_McMurry_reactions">Intramolecular McMurry reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cycloalkene&action=edit&section=11" title="Edit section: Intramolecular McMurry reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When two carbonyl groups are coupled and undergo a <a href="/wiki/McMurry_reaction" title="McMurry reaction">McMurry reaction</a>, there is a possibility of the formation of cycloalkenes under specific conditions.<sup id="cite_ref-:0_11-4" class="reference"><a href="#cite_note-:0-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> When both carbonyls are within the same molecule and not sufficiently separated from each other, a cycloalkene can be formed through an intramolecular McMurry reaction.<sup id="cite_ref-:0_11-5" class="reference"><a href="#cite_note-:0-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:McMurry_reaction_of_hexanedial.svg" class="mw-file-description"><img alt="Formation of a cycloalkane via an Intramolecular McMurry Reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/McMurry_reaction_of_hexanedial.svg/220px-McMurry_reaction_of_hexanedial.svg.png" decoding="async" width="220" height="65" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/McMurry_reaction_of_hexanedial.svg/330px-McMurry_reaction_of_hexanedial.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/McMurry_reaction_of_hexanedial.svg/440px-McMurry_reaction_of_hexanedial.svg.png 2x" data-file-width="672" data-file-height="200" /></a><figcaption></figcaption></figure> <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=Cycloalkene&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Perfluorocycloalkene" title="Perfluorocycloalkene">Perfluorocycloalkene</a> (PFCA)</li> <li><a href="/wiki/Alicyclic_compound" title="Alicyclic compound">Alicyclic compound</a></li> <li><a href="/wiki/Olefin" class="mw-redirect" title="Olefin">Olefin</a></li> <li><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkyne</a></li> <li><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkane</a></li> <li><a href="/wiki/White_spirit" title="White spirit">White spirit</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=Cycloalkene&action=edit&section=13" 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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></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 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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 class="mw-selflink selflink">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 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" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Cycloalkenes57" 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:Cycloalkenes" title="Template:Cycloalkenes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cycloalkenes" title="Template talk:Cycloalkenes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cycloalkenes" title="Special:EditPage/Template:Cycloalkenes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cycloalkenes57" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Cycloalkenes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alkene" title="Alkene">Alkenes</a></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/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:1%"><a href="/wiki/Diene" title="Diene">Dienes</a></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/Cyclobutadiene" title="Cyclobutadiene">Cyclobutadiene</a></li> <li><a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">Cyclopentadiene</a></li> <li>Cyclohexadiene <ul><li><a href="/wiki/1,3-Cyclohexadiene" class="mw-redirect" title="1,3-Cyclohexadiene">1,3-Cyclohexadiene</a></li> <li><a href="/wiki/1,4-Cyclohexadiene" class="mw-redirect" title="1,4-Cyclohexadiene">1,4-Cyclohexadiene</a></li></ul></li> <li>Cycloheptadiene <ul><li><a href="/wiki/1,3-Cycloheptadiene" title="1,3-Cycloheptadiene">1,3-Cycloheptadiene</a></li> <li><a href="/wiki/1,4-Cycloheptadiene" title="1,4-Cycloheptadiene">1,4-Cycloheptadiene</a></li></ul></li> <li><a href="/wiki/Cyclooctadiene" title="Cyclooctadiene">Cyclooctadiene</a> <ul><li><a href="/wiki/1,5-Cyclooctadiene" title="1,5-Cyclooctadiene">1,5-Cyclooctadiene</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triene" class="mw-redirect" title="Triene">Trienes</a></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/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">Cycloheptatriene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tetraenes</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/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclononatetraene" title="Cyclononatetraene">Cyclononatetraene</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: 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