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class="vector-toc-numb">2</span> <span>Structure and bonding</span> </div> </a> <ul id="toc-Structure_and_bonding-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Synthesis</span> </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Natural_occurrence" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Natural_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Natural occurrence</span> </div> </a> <ul id="toc-Natural_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Reactions</span> </div> </a> <ul id="toc-Reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyclooctatetraenide_as_a_ligand_and_ligand_precursor" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Cyclooctatetraenide_as_a_ligand_and_ligand_precursor"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Cyclooctatetraenide as a ligand and ligand precursor</span> </div> </a> <ul id="toc-Cyclooctatetraenide_as_a_ligand_and_ligand_precursor-sublist" class="vector-toc-list"> </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">7</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">8</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" > <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 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Available in 21 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-21" 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">21 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%AD%D9%84%D9%82%D9%8A_%D8%A7%D9%84%D8%A3%D9%88%D9%83%D8%AA%D8%A7%D8%AA%D8%AA%D8%B1%D8%A7%D9%8A%D9%8A%D9%86" title="حلقي الأوكتاتترايين – Arabic" lang="ar" hreflang="ar" data-title="حلقي الأوكتاتترايين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%DB%8C%DA%A9%D9%84%D9%88_%D8%A7%D9%88%DA%A9%D8%AA%D8%A7%D8%AA%D8%AA%D8%B1%D8%A7%D8%A7%D9%86" title="سیکلو اوکتاتتراان – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیکلو اوکتاتتراان" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Cyklooktatetraen" title="Cyklooktatetraen – Czech" lang="cs" hreflang="cs" data-title="Cyklooktatetraen" 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/Cyclooctatetraen" title="Cyclooctatetraen – German" lang="de" hreflang="de" data-title="Cyclooctatetraen" 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/Ciclooctatetraeno" title="Ciclooctatetraeno – Spanish" lang="es" hreflang="es" data-title="Ciclooctatetraeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</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%A7%DA%A9%D8%AA%D8%A7%D8%AA%D8%AA%D8%B1%D8%A7%D8%A7%D9%86" title="سیکلواکتاتتراان – Persian" lang="fa" hreflang="fa" data-title="سیکلواکتاتتراان" 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/Cyclooctat%C3%A9tra%C3%A8ne" title="Cyclooctatétraène – French" lang="fr" hreflang="fr" data-title="Cyclooctatétraène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Cicloottatetraene" title="Cicloottatetraene – Italian" lang="it" hreflang="it" data-title="Cicloottatetraene" 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/Ciklooktatetra%C3%A9n" title="Ciklooktatetraén – Hungarian" lang="hu" hreflang="hu" data-title="Ciklooktatetraén" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyclo-octatetraeen" title="Cyclo-octatetraeen – Dutch" lang="nl" hreflang="nl" data-title="Cyclo-octatetraeen" 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%AA%E3%82%AF%E3%82%BF%E3%83%86%E3%83%88%E3%83%A9%E3%82%A8%E3%83%B3" title="シクロオクタテトラエン – Japanese" lang="ja" hreflang="ja" data-title="シクロオクタテトラエン" 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/Siklooktatetraen" title="Siklooktatetraen – Uzbek" lang="uz" hreflang="uz" data-title="Siklooktatetraen" 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/Cyklooktatetraen" title="Cyklooktatetraen – Polish" lang="pl" hreflang="pl" data-title="Cyklooktatetraen" 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/Ciclooctatetraeno" title="Ciclooctatetraeno – Portuguese" lang="pt" hreflang="pt" data-title="Ciclooctatetraeno" 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/Ciclooctatetraen%C4%83" title="Ciclooctatetraenă – Romanian" lang="ro" hreflang="ro" data-title="Ciclooctatetraenă" 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%BE%D0%BA%D1%82%D0%B0%D1%82%D0%B5%D1%82%D1%80%D0%B0%D0%B5%D0%BD" title="Циклооктатетраен – Russian" lang="ru" hreflang="ru" data-title="Циклооктатетраен" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Ciklooktatetraen" title="Ciklooktatetraen – Serbian" lang="sr" hreflang="sr" data-title="Ciklooktatetraen" 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/Ciklooktatetraen" title="Ciklooktatetraen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ciklooktatetraen" 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/Syklo-oktatetraeeni" title="Syklo-oktatetraeeni – Finnish" lang="fi" hreflang="fi" data-title="Syklo-oktatetraeeni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</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%BE%D0%BA%D1%82%D0%B0%D1%82%D0%B5%D1%82%D1%80%D0%B0%D1%94%D0%BD" title="Циклооктатетраєн – Ukrainian" lang="uk" hreflang="uk" data-title="Циклооктатетраєн" data-language-autonym="Українська" data-language-local-name="Ukrainian" 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<tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cyclooctatetraen.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Cyclooctatetraen.svg/100px-Cyclooctatetraen.svg.png" decoding="async" width="100" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Cyclooctatetraen.svg/150px-Cyclooctatetraen.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Cyclooctatetraen.svg/200px-Cyclooctatetraen.svg.png 2x" data-file-width="108" data-file-height="108" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cyclooctatetraene-from-xtal-side-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/Cyclooctatetraene-from-xtal-side-3D-bs-17.png/120px-Cyclooctatetraene-from-xtal-side-3D-bs-17.png" decoding="async" width="120" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/Cyclooctatetraene-from-xtal-side-3D-bs-17.png/180px-Cyclooctatetraene-from-xtal-side-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a7/Cyclooctatetraene-from-xtal-side-3D-bs-17.png/240px-Cyclooctatetraene-from-xtal-side-3D-bs-17.png 2x" data-file-width="3000" data-file-height="1718" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cyclooctatetraene-from-xtal-top-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Cyclooctatetraene-from-xtal-top-3D-bs-17.png/150px-Cyclooctatetraene-from-xtal-top-3D-bs-17.png" decoding="async" width="150" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Cyclooctatetraene-from-xtal-top-3D-bs-17.png/225px-Cyclooctatetraene-from-xtal-top-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/17/Cyclooctatetraene-from-xtal-top-3D-bs-17.png/300px-Cyclooctatetraene-from-xtal-top-3D-bs-17.png 2x" data-file-width="2345" data-file-height="2345" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cyclooctatetraene-from-xtal-top-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Cyclooctatetraene-from-xtal-top-3D-sf.png/150px-Cyclooctatetraene-from-xtal-top-3D-sf.png" decoding="async" width="150" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Cyclooctatetraene-from-xtal-top-3D-sf.png/225px-Cyclooctatetraene-from-xtal-top-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Cyclooctatetraene-from-xtal-top-3D-sf.png/300px-Cyclooctatetraene-from-xtal-top-3D-sf.png 2x" data-file-width="2364" data-file-height="2364" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Cycloocta-1,3,5,7-tetraene<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">[8]Annulene<br />(1<i>Z</i>,3<i>Z</i>,5<i>Z</i>,7<i>Z</i>)-Cycloocta-1,3,5,7-tetraene<br />1,3,5,7-Cyclooctatetraene<br />COT</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=629-20-9">629-20-9</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C1%3DC%5CC%3DC%2FC%3DC%5CC%3DC1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=47034">CHEBI:47034</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.553448.html">553448</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.010.074">100.010.074</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q900926#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>211-080-3</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/637866">637866</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/AJ19R479CQ">AJ19R479CQ</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9060867">DTXSID9060867</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q900926#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C8H8/c1-2-4-6-8-7-5-3-1/h1-8H/b2-1-,3-1-,4-2-,5-3-,6-4-,7-5-,8-6-,8-7-<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KDUIUFJBNGTBMD-BONZMOEMSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C8H8/c1-2-4-6-8-7-5-3-1/h1-8H/b2-1-,3-1-,4-2-,5-3-,6-4-,7-5-,8-6-,8-7-</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KDUIUFJBNGTBMD-BONZMOEMBR</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C1=C\C=C/C=C\C=C1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>8</sub>H<sub>8</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>104.15 g/mol    </td></tr> <tr> <td>Appearance </td> <td>Clear yellow </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.9250 g/cm<sup>3</sup>, liquid </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−5 to −3 °C (23 to 27 °F; 268 to 270 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>142 to 143 °C (288 to 289 °F; 415 to 416 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>immiscible </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>-53.9·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H225: Highly flammable liquid and vapour">H225</abbr>, <abbr class="abbr" title="H304: May be fatal if swallowed and enters airways">H304</abbr>, <abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P240: Ground and bond container and receiving equipment.">P240</abbr>, <abbr class="abbr" title="P241: Use explosion-proof electrical/ventilating/light/.../equipment.">P241</abbr>, <abbr class="abbr" title="P242: Use only non-sparking tools.">P242</abbr>, <abbr class="abbr" title="P243: Take precautionary measures to prevent static discharges.">P243</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.">P301+P310</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P331: Do NOT induce vomiting.">P331</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P370+P378: In case of fire: Use ... to extinguish.">P370+P378</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P403+P235: Store in a well ventilated place. Keep cool.">P403+P235</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_e7ff6424fc1bdd38" /></span><map name="ImageMap_e7ff6424fc1bdd38"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>−11 °C (12 °F; 262 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>561 °C (1,042 °F; 834 K) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a></div> </td> <td><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a><br /><a href="/wiki/Tetraphenylene" title="Tetraphenylene">Tetraphenylene</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=444042371&page2=Cyclooctatetraene">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>1,3,5,7-Cyclooctatetraene</b> (<b>COT</b>) is an <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">unsaturated</a> <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivative</a> of <a href="/wiki/Cyclooctane" title="Cyclooctane">cyclooctane</a>, with the formula C<sub>8</sub>H<sub>8</sub>. It is also known as [8]<a href="/wiki/Annulene" title="Annulene">annulene</a>. This polyunsaturated <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> is a colorless to light yellow flammable liquid at room temperature. Because of its <a href="/wiki/Stoichiometry" title="Stoichiometry">stoichiometric</a> relationship to <a href="/wiki/Benzene" title="Benzene">benzene</a>, COT has been the subject of much research and some controversy. </p><p>Unlike benzene, C<sub>6</sub>H<sub>6</sub>, cyclooctatetraene, C<sub>8</sub>H<sub>8</sub>, is not <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a>, although its <a href="/wiki/Dianion" title="Dianion">dianion</a>, <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">8</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">8</sub></span></span></span> (<a href="/wiki/Cyclooctatetraenide_anion" title="Cyclooctatetraenide anion">cyclooctatetraenide</a>), is. Its reactivity is characteristic of an ordinary <a href="/wiki/Polyene" title="Polyene">polyene</a>, i.e. it undergoes <a href="/wiki/Addition_reaction" title="Addition reaction">addition reactions</a>. Benzene, by contrast, characteristically undergoes <a href="/wiki/Substitution_reaction" title="Substitution reaction">substitution reactions</a>, not additions. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclooctatetraene&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>1,3,5,7-Cyclooctatetraene was initially synthesized by <a href="/wiki/Richard_Willst%C3%A4tter" title="Richard Willstätter">Richard Willstätter</a> in Munich in 1905 using <a href="/wiki/Pseudopelletierine" title="Pseudopelletierine">pseudopelletierine</a> as the starting material and the <a href="/wiki/Hofmann_elimination" title="Hofmann elimination">Hofmann elimination</a> as the key transformation:<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><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><span typeof="mw:File"><a href="/wiki/File:Willstaetter_Synthesis_COT.svg" class="mw-file-description" title="Willstätter's synthesis of cyclooctatetraene (1905)."><img alt="Willstätter's synthesis of cyclooctatetraene (1905)." src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Willstaetter_Synthesis_COT.svg/450px-Willstaetter_Synthesis_COT.svg.png" decoding="async" width="450" height="244" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Willstaetter_Synthesis_COT.svg/675px-Willstaetter_Synthesis_COT.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Willstaetter_Synthesis_COT.svg/900px-Willstaetter_Synthesis_COT.svg.png 2x" data-file-width="1085" data-file-height="588" /></a></span></dd></dl> <p>Willstätter noted that the compound did not exhibit the expected aromaticity. Between 1939 and 1943, chemists throughout the US unsuccessfully attempted to synthesize COT. They rationalized their lack of success with the conclusion that Willstätter had not actually synthesized the compound but instead its isomer, <a href="/wiki/Styrene" title="Styrene">styrene</a>. Willstätter responded to these reviews in his autobiography, where he noted that the American chemists were 'untroubled' by the reduction of his cyclooctatetraene to cyclooctane (a reaction impossible for styrene). During <a href="/wiki/World_War_II" title="World War II">World War II</a>, <a href="/wiki/Walter_Reppe" title="Walter Reppe">Walter Reppe</a> at <a href="/wiki/BASF" title="BASF">BASF</a> Ludwigshafen developed a simple, one-step synthesis of cyclooctatetraene from acetylene, providing material identical to that prepared by Willstätter.<sup id="cite_ref-reppe_4-0" class="reference"><a href="#cite_note-reppe-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Any remaining doubts on the accuracy of Willstätter's original synthesis were resolved when Arthur C. Cope and co-workers at <a href="/wiki/MIT" class="mw-redirect" title="MIT">MIT</a> reported, in 1947, a complete repetition of the Willstätter synthesis, step by step, using the originally reported techniques. They obtained the same cyclooctatetraene,<sup id="cite_ref-house1_5-0" class="reference"><a href="#cite_note-house1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> and they subsequently reported modern spectral characterization of many of the intermediate products, again confirming the accuracy of Willstätter's original work.<sup id="cite_ref-house2_6-0" class="reference"><a href="#cite_note-house2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> However, the freezing temperature of the product was different from pure COT, and the authors interpreted it as contamination with about 30% of styrene. </p> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclooctatetraene&action=edit&section=2" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:All-Z-Cyclooctatetraene_3D_skeletal_formula.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/All-Z-Cyclooctatetraene_3D_skeletal_formula.svg/180px-All-Z-Cyclooctatetraene_3D_skeletal_formula.svg.png" decoding="async" width="180" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/All-Z-Cyclooctatetraene_3D_skeletal_formula.svg/270px-All-Z-Cyclooctatetraene_3D_skeletal_formula.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/03/All-Z-Cyclooctatetraene_3D_skeletal_formula.svg/360px-All-Z-Cyclooctatetraene_3D_skeletal_formula.svg.png 2x" data-file-width="234" data-file-height="174" /></a><figcaption>Cyclooctatetraene in its native "tub-shaped" conformation</figcaption></figure> <p>Early studies demonstrated that COT did not display the chemistry of an aromatic compound.<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> Then, early electron diffraction experiments concluded that the C-C bond distances were identical.<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> However, X-ray diffraction data from H. S. Kaufman demonstrated cyclooctatetraene to adopt several <a href="/wiki/Conformation_(chemistry)" class="mw-redirect" title="Conformation (chemistry)">conformations</a> and to contain two distinct C–C bond distances.<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 result indicated that COT is an <a href="/wiki/Annulene" title="Annulene">annulene</a> with fixed alternating single and double C-C bonds. </p><p>In its normal state, cyclooctatetraene is non-planar and adopts a <b>tub conformation</b> with angles C=C−C = 126.1° and C=C−H = 117.6°.<sup id="cite_ref-Thomas_10-0" class="reference"><a href="#cite_note-Thomas-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The point group of cyclooctatetraene is D<sub>2d</sub>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>In its planar transition state, the D<sub>4h</sub> transitional state is more stable than the D<sub>8h</sub> transitional state due to the <a href="/wiki/Jahn%E2%80%93Teller_effect" title="Jahn–Teller effect">Jahn–Teller effect</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclooctatetraene&action=edit&section=3" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Richard Willstätter's original synthesis (4 consecutive <a href="/wiki/Elimination_reaction" title="Elimination reaction">elimination reactions</a> on a cyclooctane framework) gives relatively low yields. Reppe's synthesis of cyclooctatetraene, which involves treating <a href="/wiki/Acetylene" title="Acetylene">acetylene</a> at high pressure with a warm mixture of <a href="/wiki/Nickel_dicyanide" title="Nickel dicyanide">nickel cyanide</a> and <a href="/wiki/Calcium_carbide" title="Calcium carbide">calcium carbide</a>, was much better, with <a href="/wiki/Chemical_yield" class="mw-redirect" title="Chemical yield">chemical yields</a> near 90%:<sup id="cite_ref-reppe_4-1" class="reference"><a href="#cite_note-reppe-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Reppe_Synthesis_COT.svg" class="mw-file-description" title="Reppe's synthesis of cyclooctatetraene"><img alt="Reppe's synthesis of cyclooctatetraene" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Reppe_Synthesis_COT.svg/330px-Reppe_Synthesis_COT.svg.png" decoding="async" width="330" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Reppe_Synthesis_COT.svg/495px-Reppe_Synthesis_COT.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/26/Reppe_Synthesis_COT.svg/660px-Reppe_Synthesis_COT.svg.png 2x" data-file-width="603" data-file-height="193" /></a></span></dd></dl> <p>COT can also be prepared by <a href="/wiki/Photolysis" class="mw-redirect" title="Photolysis">photolysis</a> of <a href="/wiki/Barrelene" title="Barrelene">barrelene</a>, one of its <a href="/wiki/Structural_isomer" title="Structural isomer">structural isomers</a>, the reaction proceeding via another isolable isomer, <a href="/wiki/Bullvalene#Semibullvalene" title="Bullvalene">semibullvalene</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> COT derivatives can also be synthesised by way of semibullvalene intermediates. In the sequence illustrated below, octaethylcyclooctatetraene (C<sub>8</sub><a href="/wiki/Ethyl_group" title="Ethyl group">Et</a><sub>8</sub>) is formed by <a href="/wiki/Isomerisation" class="mw-redirect" title="Isomerisation">thermal isomerisation</a> of octaethylsemibullvalene, itself formed by <a href="/wiki/Copper(I)_bromide" title="Copper(I) bromide">copper(I) bromide</a> mediated <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">cyclodimerisation</a> of 1,2,3,4-tetraethyl-1,4-dilithio-1,3-butadiene.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File/Frameless"><a href="/wiki/File:NewSemibullvaleneSynthesis.png" class="mw-file-description" title="Synthesis of octaethylsemibullvalene from 1,2,3,4-tetraethyl-1,4-diiodo-1,3-butadiene and its thermal isomerisation to octaethylcyclooctatetraene"><img alt="Synthesis of octaethylsemibullvalene from 1,2,3,4-tetraethyl-1,4-diiodo-1,3-butadiene and its thermal isomerisation to octaethylcyclooctatetraene" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/NewSemibullvaleneSynthesis.png/600px-NewSemibullvaleneSynthesis.png" decoding="async" width="600" height="250" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/NewSemibullvaleneSynthesis.png/900px-NewSemibullvaleneSynthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/b/b7/NewSemibullvaleneSynthesis.png 2x" data-file-width="978" data-file-height="408" /></a></span></dd></dl> <p>Because COT is unstable and easily forms explosive <a href="/wiki/Organic_peroxide" class="mw-redirect" title="Organic peroxide">organic peroxides</a>, a small amount of <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinone</a> is usually added to commercially available material. Testing for peroxides is advised when using a previously opened bottle; white crystals around the neck of the bottle may be composed of the peroxide, which may explode when mechanically disturbed. </p> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclooctatetraene&action=edit&section=4" title="Edit section: Natural occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyclooctatetraene has been isolated from certain fungi.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclooctatetraene&action=edit&section=5" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The π bonds in COT react as usual for olefins, rather than as aromatic ring systems. Mono- and poly<a href="/wiki/Epoxide" title="Epoxide">epoxides</a> can be generated by reaction of COT with <a href="/wiki/Peroxy_acid" title="Peroxy acid">peroxy acids</a> or with <a href="/wiki/Dimethyldioxirane" title="Dimethyldioxirane">dimethyldioxirane</a>. Various other addition reactions are also known. Furthermore, <a href="/wiki/Polyacetylene" title="Polyacetylene">polyacetylene</a> can be synthesized via the <a href="/wiki/Ring-opening_polymerization" title="Ring-opening polymerization">ring-opening polymerization</a> of cyclooctatetraene.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> COT itself—and also analogs with side-chains—have been used as metal ligands and in <a href="/wiki/Sandwich_compound" title="Sandwich compound">sandwich compounds</a>. </p><p>Cyclooctatetraene also undergoes <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearrangement reactions</a> to form <a href="/wiki/Aromatic_ring" class="mw-redirect" title="Aromatic ring">aromatic ring</a> systems. For instance, <a href="/wiki/Organic_redox_reaction" title="Organic redox reaction">oxidation</a> with <a href="/wiki/Aqueous" class="mw-redirect" title="Aqueous">aqueous</a> <a href="/wiki/Mercury(II)_sulfate" title="Mercury(II) sulfate">mercury(II) sulfate</a> forms <a href="/wiki/Phenylacetaldehyde" title="Phenylacetaldehyde">phenylacetaldehyde</a><sup id="cite_ref-reppe_4-2" class="reference"><a href="#cite_note-reppe-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Photochemistry#Organic_photochemistry" title="Photochemistry">photochemical</a> rearrangement of its mono<a href="/wiki/Epoxide" title="Epoxide">epoxide</a> forms <a href="/wiki/Benzofuran" title="Benzofuran">benzofuran</a>.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Cyclooctatetraenide_as_a_ligand_and_ligand_precursor">Cyclooctatetraenide as a ligand and ligand precursor</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclooctatetraene&action=edit&section=6" title="Edit section: Cyclooctatetraenide as a ligand and ligand precursor"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cyclooctatetraenide_anion" title="Cyclooctatetraenide anion">Cyclooctatetraenide anion</a></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Cyclooctatetraenide-3D-ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Cyclooctatetraenide-3D-ball.png/200px-Cyclooctatetraenide-3D-ball.png" decoding="async" width="200" height="160" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Cyclooctatetraenide-3D-ball.png/300px-Cyclooctatetraenide-3D-ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Cyclooctatetraenide-3D-ball.png/400px-Cyclooctatetraenide-3D-ball.png 2x" data-file-width="1100" data-file-height="882" /></a><figcaption><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a> of COT<sup>2−</sup></figcaption></figure> <p>COT readily reacts with <a href="/wiki/Potassium" title="Potassium">potassium</a> metal to form the salt K<sub>2</sub>COT, which contains the dianion <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">8</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">8</sub></span></span></span>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The dianion is planar, octagonal, and <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> with a <a href="/wiki/H%C3%BCckel_rule" class="mw-redirect" title="Hückel rule">Hückel electron count</a> of 10. </p><p>Cyclooctatetraene forms <a href="/wiki/Organometallic_chemistry#Organometallic_compounds" title="Organometallic chemistry">organometallic complexes</a> with some metals, including <a href="/wiki/Yttrium" title="Yttrium">yttrium</a>, <a href="/wiki/Lanthanide" title="Lanthanide">lanthanides</a>, and actinides.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Sandwich_compound" title="Sandwich compound">sandwich compound</a> <a href="/wiki/Uranocene" title="Uranocene">uranocene</a> (U(COT)<sub>2</sub>) features two <a href="/wiki/Hapticity" title="Hapticity">η<sup>8</sup></a>-COT ligands. In <a href="/wiki/Bis(cyclooctatetraene)iron" title="Bis(cyclooctatetraene)iron">bis(cyclooctatetraene)iron</a> (Fe(COT)<sub>2</sub>) one COT is η<sup>6</sup> and the other is η<sup>4</sup>. <a href="/wiki/(Cyclooctatetraene)iron_tricarbonyl" title="(Cyclooctatetraene)iron tricarbonyl">(Cyclooctatetraene)iron tricarbonyl</a> features η<sup>4</sup>-COT. The room-temperature <sup>1</sup>H NMR spectra of these iron complexes are singlets, indicative of <a href="/wiki/Fluxionality" class="mw-redirect" title="Fluxionality">fluxionality</a>.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Uranocene-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Uranocene-3D-vdW.png/220px-Uranocene-3D-vdW.png" decoding="async" width="220" height="248" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Uranocene-3D-vdW.png/330px-Uranocene-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Uranocene-3D-vdW.png/440px-Uranocene-3D-vdW.png 2x" data-file-width="975" data-file-height="1100" /></a><figcaption><a href="/wiki/Uranocene" title="Uranocene">Uranocene</a>, a <a href="/wiki/Sandwich_compound" title="Sandwich compound">sandwich compound</a> containing two COT<sup>2−</sup> rings.</figcaption></figure> <p>Cyclooctatetraene is <a href="/wiki/Chlorinated" class="mw-redirect" title="Chlorinated">chlorinated</a> to give a [4.2.0]-<a href="/wiki/Bicyclic" class="mw-redirect" title="Bicyclic">bicyclic</a> compound, which reacts further with <a href="/wiki/Dimethyl_acetylenedicarboxylate" title="Dimethyl acetylenedicarboxylate">dimethyl acetylenedicarboxylate</a> in a <a href="/wiki/Diels-Alder_reaction" class="mw-redirect" title="Diels-Alder reaction">Diels-Alder reaction</a> (DA). Retro-DA at 200 °C releases cis-dichlorocyclobutene. This compound reacts with <a href="/wiki/Diiron_nonacarbonyl" title="Diiron nonacarbonyl">diiron nonacarbonyl</a> to give <a href="/wiki/Cyclobutadieneiron_tricarbonyl" title="Cyclobutadieneiron tricarbonyl">cyclobutadieneiron tricarbonyl</a>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:CyclobutadieneirontricarbonylSynthesis.png" class="mw-file-description" title="Cyclobutadieneiron tricarbonyl Synthesis"><img alt="Cyclobutadieneiron tricarbonyl Synthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/CyclobutadieneirontricarbonylSynthesis.png/600px-CyclobutadieneirontricarbonylSynthesis.png" decoding="async" width="600" height="328" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/CyclobutadieneirontricarbonylSynthesis.png/900px-CyclobutadieneirontricarbonylSynthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/3/3b/CyclobutadieneirontricarbonylSynthesis.png 2x" data-file-width="970" data-file-height="531" /></a></span></dd></dl> <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=Cyclooctatetraene&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Barrelene" title="Barrelene">Barrelene</a>, <a href="/wiki/Structural_isomer" title="Structural isomer">structural isomer</a> of cyclooctatetraene</li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Cyclobutadiene" title="Cyclobutadiene">Cyclobutadiene</a></li> <li><a href="/wiki/Heptafulvene" class="mw-redirect" title="Heptafulvene">Heptafulvene</a>, <a href="/wiki/Structural_isomer" title="Structural isomer">structural isomer</a> of cyclooctatetraene</li> <li><a href="/wiki/Pentalene" title="Pentalene">Pentalene</a></li> <li><a href="/wiki/Semibullvalene" class="mw-redirect" title="Semibullvalene">Semibullvalene</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=Cyclooctatetraene&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-iupac2013-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_1-0">^</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 no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation book cs1">"Front Matter". <i>Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. 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href="/wiki/Cyclodecapentaene" title="Cyclodecapentaene">Cyclodecapentaene</a></li> <li><a href="/wiki/Cyclododecahexaene" title="Cyclododecahexaene">Cyclododecahexaene</a></li> <li><i><a href="/wiki/Cyclotetradecaheptaene" title="Cyclotetradecaheptaene">Cyclotetradecaheptaene</a></i></li> <li><a href="/wiki/Cyclohexadecaoctaene" class="mw-redirect" title="Cyclohexadecaoctaene">Cyclohexadecaoctaene</a></li> <li><i><a href="/wiki/Cyclooctadecanonaene" title="Cyclooctadecanonaene">Cyclooctadecanonaene</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Odd–numbered</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/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">Cyclopentadiene</a></li> <li><a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">Cycloheptatriene</a></li> <li><a href="/wiki/Cyclononatetraene" title="Cyclononatetraene">Cyclononatetraene</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>Compounds in <i>italics</i> are <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a></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="Cycloalkenes" 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="Cycloalkenes" style="font-size:114%;margin:0 4em"><a href="/wiki/Cycloalkene" title="Cycloalkene">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" 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