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class="vector-toc-numb">2</span> <span>Structures and bonding</span> </div> </a> <ul id="toc-Structures_and_bonding-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactivity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reactivity</span> </div> </a> <button aria-controls="toc-Reactivity-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactivity subsection</span> </button> <ul id="toc-Reactivity-sublist" class="vector-toc-list"> <li id="toc-Singlet-triplet_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Singlet-triplet_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Singlet-triplet effects</span> </div> </a> <ul id="toc-Singlet-triplet_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyclopropanation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cyclopropanation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Cyclopropanation</span> </div> </a> <ul id="toc-Cyclopropanation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-C—H_insertion" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#C—H_insertion"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>C—H insertion</span> </div> </a> <ul id="toc-C—H_insertion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Electrophilic_attack" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Electrophilic_attack"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Electrophilic attack</span> </div> </a> <ul id="toc-Electrophilic_attack-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carbene_dimerization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carbene_dimerization"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Carbene dimerization</span> </div> </a> <ul id="toc-Carbene_dimerization-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Ligands_in_organometallic_chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Ligands_in_organometallic_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Ligands in organometallic chemistry</span> </div> </a> <ul id="toc-Ligands_in_organometallic_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Industrial_applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Industrial_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Industrial applications</span> </div> </a> <ul id="toc-Industrial_applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>History</span> </div> </a> <ul id="toc-History-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> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" 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Available in 32 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-32" 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">32 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D8%B1%D8%A8%D9%8A%D9%86" title="كربين – Arabic" lang="ar" hreflang="ar" data-title="كربين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Karben" title="Karben – Bosnian" lang="bs" hreflang="bs" data-title="Karben" 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/Carb%C3%A8" title="Carbè – Catalan" lang="ca" hreflang="ca" data-title="Carbè" 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/Karbeny" title="Karbeny – Czech" lang="cs" hreflang="cs" data-title="Karbeny" 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/Carbene" title="Carbene – German" lang="de" hreflang="de" data-title="Carbene" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CE%B1%CF%81%CE%B2%CE%AD%CE%BD%CE%B9%CE%B1" title="Καρβένια – Greek" lang="el" hreflang="el" data-title="Καρβένια" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Carbeno" title="Carbeno – Spanish" lang="es" hreflang="es" data-title="Carbeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Karbeno" title="Karbeno – Esperanto" lang="eo" hreflang="eo" data-title="Karbeno" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Karbeno" title="Karbeno – Basque" lang="eu" hreflang="eu" data-title="Karbeno" 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/%DA%A9%D8%A7%D8%B1%D8%A8%D9%86_(%D8%B4%DB%8C%D9%85%DB%8C)" title="کاربن (شیمی) – Persian" lang="fa" hreflang="fa" data-title="کاربن (شیمی)" 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/Carb%C3%A8ne" title="Carbène – French" lang="fr" hreflang="fr" data-title="Carbène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Carbeno" title="Carbeno – Galician" lang="gl" hreflang="gl" data-title="Carbeno" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%B9%B4%EB%B2%A4" title="카벤 – Korean" lang="ko" hreflang="ko" data-title="카벤" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Carbene" title="Carbene – Italian" lang="it" hreflang="it" data-title="Carbene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%B5%D0%BD%D0%B4%D0%B5%D1%80" title="Карбендер – Kazakh" lang="kk" hreflang="kk" data-title="Карбендер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Karb%C3%A9n" title="Karbén – Hungarian" lang="hu" hreflang="hu" data-title="Karbén" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-fj mw-list-item"><a href="https://fj.wikipedia.org/wiki/Kasamuni" title="Kasamuni – Fijian" lang="fj" hreflang="fj" data-title="Kasamuni" data-language-autonym="Na Vosa Vakaviti" data-language-local-name="Fijian" class="interlanguage-link-target"><span>Na Vosa Vakaviti</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Carbeen" title="Carbeen – Dutch" lang="nl" hreflang="nl" data-title="Carbeen" 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%AB%E3%83%AB%E3%83%99%E3%83%B3" title="カルベン – Japanese" lang="ja" hreflang="ja" data-title="カルベン" 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/Karbenlar" title="Karbenlar – Uzbek" lang="uz" hreflang="uz" data-title="Karbenlar" 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-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%95%E0%A8%BE%E0%A8%B0%E0%A8%AC%E0%A9%80%E0%A8%A8" title="ਕਾਰਬੀਨ – Punjabi" lang="pa" hreflang="pa" data-title="ਕਾਰਬੀਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Karbeny_(rodniki)" title="Karbeny (rodniki) – Polish" lang="pl" hreflang="pl" data-title="Karbeny (rodniki)" 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/Carbenos" title="Carbenos – Portuguese" lang="pt" hreflang="pt" data-title="Carbenos" 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/Carben%C4%83" title="Carbenă – Romanian" lang="ro" hreflang="ro" data-title="Carbenă" 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%9A%D0%B0%D1%80%D0%B1%D0%B5%D0%BD%D1%8B" title="Карбены – Russian" lang="ru" hreflang="ru" data-title="Карбены" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-skr mw-list-item"><a href="https://skr.wikipedia.org/wiki/%DA%A9%D8%A7%D8%B1%D8%A8%DB%8C%D9%86" title="کاربین – Saraiki" lang="skr" hreflang="skr" data-title="کاربین" data-language-autonym="سرائیکی" data-language-local-name="Saraiki" class="interlanguage-link-target"><span>سرائیکی</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Carbene" title="Carbene – Simple English" lang="en-simple" hreflang="en-simple" data-title="Carbene" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Karbeenit" title="Karbeenit – Finnish" lang="fi" hreflang="fi" data-title="Karbeenit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AE%BE%E0%AE%AA%E0%AF%80%E0%AE%A9%E0%AF%8D" title="காபீன் – Tamil" lang="ta" hreflang="ta" data-title="காபீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%84%E0%B8%B2%E0%B8%A3%E0%B9%8C%E0%B8%9A%E0%B8%B5%E0%B8%99" title="คาร์บีน – Thai" lang="th" hreflang="th" data-title="คาร์บีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%B5%D0%BD%D0%B8" title="Карбени – Ukrainian" lang="uk" hreflang="uk" data-title="Карбени" 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/%E5%8D%A1%E5%AE%BE" title="卡宾 – Chinese" lang="zh" hreflang="zh" data-title="卡宾" 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free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic molecule containing a neutral carbon with two unbound valence electrons</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the chemical class. For the compound, see <a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene (compound)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Carbine" title="Carbine">carbine</a> or <a href="/wiki/Carbyne" title="Carbyne">carbyne</a>.</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Carbene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Carbene.svg/60px-Carbene.svg.png" decoding="async" width="60" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Carbene.svg/90px-Carbene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Carbene.svg/120px-Carbene.svg.png 2x" data-file-width="512" data-file-height="1051" /></a><figcaption><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a> is the simplest carbene.</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>carbene</b> is a <a href="/wiki/Molecule" title="Molecule">molecule</a> containing a neutral <a href="/wiki/Carbon" title="Carbon">carbon</a> atom with a <a href="/wiki/Valence_(chemistry)" title="Valence (chemistry)">valence</a> of two and two unshared <a href="/wiki/Valence_electron" title="Valence electron">valence electrons</a>. The general formula is <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">R−:C−R'</span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R=C:</span> where the R represents <a href="/wiki/Substituent" title="Substituent">substituents</a> or hydrogen atoms. </p><p>The term "carbene" may also refer to the specific compound <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">:CH<sub class="template-chem2-sub">2</sub></span>, also called <a href="/wiki/Methylene_radical" class="mw-redirect" title="Methylene radical">methylene</a>, the parent <a href="/wiki/Hydride" title="Hydride">hydride</a> from which all other carbene compounds are formally derived.<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><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> </p><p>There are two types of carbenes: <a href="/wiki/Singlet_state" title="Singlet state">singlets</a> or <a href="/wiki/Triplet_state" title="Triplet state">triplets</a>, depending upon their electronic structure.<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> The different classes undergo different reactions. </p><p>Most carbenes are extremely reactive and short-lived. A small number (the di<a href="/wiki/Halogen" title="Halogen">halo</a>carbenes, <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a>,<sup id="cite_ref-FOOTNOTEGrossman200335_4-0" class="reference"><a href="#cite_note-FOOTNOTEGrossman200335-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">carbon monosulfide</a>) can be isolated, and can stabilize as <a href="/wiki/Coordination_complex" title="Coordination complex">metal ligands</a>, but otherwise cannot be stored in bulk. A rare exception are the <a href="/wiki/Persistent_carbene" title="Persistent carbene">persistent carbenes</a>,<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> which have extensive application in modern <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Generation">Generation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbene&action=edit&section=1" title="Edit section: Generation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are two common methods for carbene generation. </p><p>In <a href="/wiki/Alpha_elimination" title="Alpha elimination">α elimination</a>, two substituents eliminate from the same carbon atom. This occurs with reagents with no good <a href="/wiki/Leaving_group" title="Leaving group">leaving groups</a> vicinal to an acidic proton are exposed to strong base; for example, <a href="/wiki/Phenyllithium" title="Phenyllithium">phenyllithium</a> will abstract <a href="/wiki/Hydrohalic_acid" class="mw-redirect" title="Hydrohalic acid">HX</a> from a <a href="/wiki/Haloform" class="mw-redirect" title="Haloform">haloform</a> (CHX<sub>3</sub>).<sup id="cite_ref-FOOTNOTEGrossman200384–85_6-0" class="reference"><a href="#cite_note-FOOTNOTEGrossman200384–85-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Such reactions typically require <a href="/wiki/Phase-transfer_catalyst" title="Phase-transfer catalyst">phase-transfer conditions</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2024)">citation needed</span></a></i>]</sup> </p><p>Molecules with no acidic proton can also form carbenes. A <a href="/wiki/Geminal" title="Geminal">geminal</a> dihalide exposed to <a href="/wiki/Organolithium_reagent" title="Organolithium reagent">organolithiums</a> can undergo <a href="/wiki/Metal-halogen_exchange" class="mw-redirect" title="Metal-halogen exchange">metal-halogen exchange</a> and then eliminate a <a href="/wiki/Lithium_salt" class="mw-redirect" title="Lithium salt">lithium salt</a> to give a carbene, and <a href="/wiki/Zinc" title="Zinc">zinc metal</a> abstracts halogens similarly in the <a href="/wiki/Simmons%E2%80%93Smith_reaction" title="Simmons–Smith reaction">Simmons–Smith reaction</a>.<sup id="cite_ref-FOOTNOTEGrossman200385_7-0" class="reference"><a href="#cite_note-FOOTNOTEGrossman200385-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>R<sub>2</sub>CBr<sub>2</sub> + BuLi → R<sub>2</sub>CLi(Br) + BuBr</dd> <dd>R<sub>2</sub>CLi(Br) → R<sub>2</sub>C + LiBr</dd></dl> <p>It remains uncertain if these conditions form truly free carbenes or a metal-carbene complex. Nevertheless, metallocarbenes so formed give the expected organic products.<sup id="cite_ref-FOOTNOTEGrossman200385_7-1" class="reference"><a href="#cite_note-FOOTNOTEGrossman200385-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In a specialized but instructive case, α-halo<a href="/wiki/Mercury_(element)" title="Mercury (element)">mercury</a> compounds can be isolated and separately thermolyzed. The "<a href="/w/index.php?title=Seyferth_reagent&action=edit&redlink=1" class="new" title="Seyferth reagent (page does not exist)">Seyferth reagent</a>" releases CCl<sub>2</sub> upon heating: </p> <dl><dd>C<sub>6</sub>H<sub>5</sub>HgCCl<sub>3</sub> → CCl<sub>2</sub> + C<sub>6</sub>H<sub>5</sub>HgCl</dd></dl> <p>Separately, carbenes can be produced from an extrusion reaction with a large free energy change. <a href="/wiki/Diazirine" title="Diazirine">Diazirines</a> and <a href="/wiki/Epoxide" title="Epoxide">epoxides</a> photolyze with a tremendous release in <a href="/wiki/Ring_strain" title="Ring strain">ring strain</a> to carbenes. The former extrude inert <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> gas, but epoxides typically give reactive <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> wastes, and <a href="/wiki/Asymmetric_synthesis" class="mw-redirect" title="Asymmetric synthesis">asymmetric</a> epoxides can potentially form two different carbenes. Typically, the C-O bond with lesser fractional bond order (fewer double-bond resonance structures) breaks. For example, when one substituent is <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> and another <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a>, the aryl-substituted carbon is usually released as a carbene fragment. </p><p> Ring strain is not necessary for a strong thermodynamic driving force. <a href="/wiki/Photolysis" class="mw-redirect" title="Photolysis">Photolysis</a>, <a href="/wiki/Heat" title="Heat">heat</a>, or <a href="/wiki/Transition_metal" title="Transition metal">transition metal</a> catalysts (typically <a href="/wiki/Rhodium" title="Rhodium">rhodium</a> and <a href="/wiki/Copper" title="Copper">copper</a>) decompose <a href="/wiki/Diazoalkane" class="mw-redirect" title="Diazoalkane">diazoalkanes</a> to a carbene and gaseous <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>; this occurs in the <a href="/wiki/Bamford%E2%80%93Stevens_reaction" title="Bamford–Stevens reaction">Bamford–Stevens reaction</a> and <a href="/wiki/Wolff_rearrangement" title="Wolff rearrangement">Wolff rearrangement</a>. As with the case of metallocarbenes, some reactions of diazoalkanes that formally proceed via carbenes may instead form a <a href="/wiki/1,3-Dipolar_cycloaddition" title="1,3-Dipolar cycloaddition">[3+2] cycloadduct</a> intermediate that extrudes nitrogen. </p><figure typeof="mw:File/Frame"><a href="/wiki/File:Alkylidene_carbene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Alkylidene_carbene.svg/512px-Alkylidene_carbene.svg.png" decoding="async" width="512" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Alkylidene_carbene.svg/768px-Alkylidene_carbene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/36/Alkylidene_carbene.svg/1024px-Alkylidene_carbene.svg.png 2x" data-file-width="512" data-file-height="80" /></a><figcaption>Alkylidene carbene</figcaption></figure><p>To generate an <a href="/wiki/Alkylidene" class="mw-redirect" title="Alkylidene">alkylidene</a> carbene a ketone can be exposed to <a href="/wiki/Trimethylsilyl" class="mw-redirect" title="Trimethylsilyl">trimethylsilyl</a> <a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a> and then a strong base. </p><div class="mw-heading mw-heading2"><h2 id="Structures_and_bonding">Structures and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbene&action=edit&section=2" title="Edit section: Structures and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Carbenes.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Carbenes.svg/220px-Carbenes.svg.png" decoding="async" width="220" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Carbenes.svg/330px-Carbenes.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Carbenes.svg/440px-Carbenes.svg.png 2x" data-file-width="512" data-file-height="197" /></a><figcaption>Singlet and triplet carbenes</figcaption></figure> <p>The two classes of carbenes are <a href="/wiki/Diradical" title="Diradical">singlet</a> and <a href="/wiki/Diradical" title="Diradical">triplet</a> carbenes. Triplet carbenes are <a href="/wiki/Diradical" title="Diradical">diradicals</a> with two unpaired electrons, typically form from reactions that break two <a href="/wiki/Sigma_bond" title="Sigma bond">σ bonds</a> (α elimination and some extrusion reactions), and do not <a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">rehybridize</a> the carbene atom. Singlet carbenes have a single <a href="/wiki/Lone_pair" title="Lone pair">lone pair</a>, typically form from diazo decompositions, and adopt an <a href="/wiki/Trigonal_planar_molecular_geometry" title="Trigonal planar molecular geometry"><i>sp</i><sup>2</sup></a> orbital structure.<sup id="cite_ref-FOOTNOTEGrossman200384_8-0" class="reference"><a href="#cite_note-FOOTNOTEGrossman200384-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Bond angles (as determined by <a href="/wiki/Electron_paramagnetic_resonance" title="Electron paramagnetic resonance">EPR</a>) are 125–140° for triplet methylene and 102° for singlet methylene. </p><p>Most carbenes have a <a href="/wiki/Bent_geometry" class="mw-redirect" title="Bent geometry">nonlinear</a> triplet ground state. For simple hydrocarbons, triplet carbenes are usually only 8 <a href="/wiki/Kilocalorie" class="mw-redirect" title="Kilocalorie">kcal</a>/<a href="/wiki/Mole_(unit)" title="Mole (unit)">mol</a> (33 <a href="/wiki/Kilojoule" class="mw-redirect" title="Kilojoule">kJ</a>/mol) more stable than singlet carbenes, comparable to <a href="/wiki/Amine#Structure" title="Amine">nitrogen inversion</a>. The stabilization is in part attributed to <a href="/wiki/Hund%27s_rule_of_maximum_multiplicity" title="Hund's rule of maximum multiplicity">Hund's rule of maximum multiplicity</a>. However, strategies to stabilize triplet carbenes at room temperature are elusive. <a href="/wiki/9-fluorenylidene" class="mw-redirect" title="9-fluorenylidene">9-Fluorenylidene</a> has been shown to be a rapidly <a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">equilibrating</a> mixture of singlet and triplet states with an approximately 1.1 kcal/mol (4.6 kJ/mol) energy difference, although extensive <a href="/wiki/Electron_delocalization" class="mw-redirect" title="Electron delocalization">electron delocalization</a> into the rings complicates any conclusions drawn from di<a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a> carbenes.<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> Simulations suggest that <a href="/wiki/Electropositive" class="mw-redirect" title="Electropositive">electropositive</a> heteroatoms can <a href="/wiki/Thermodynamic" class="mw-redirect" title="Thermodynamic">thermodynamically</a> stabilize triplet carbenes, such as in <a href="/wiki/Silyl" class="mw-redirect" title="Silyl">silyl</a> and <a href="/wiki/Silyloxy" class="mw-redirect" title="Silyloxy">silyloxy</a> carbenes, especially trifluorosilyl carbenes.<sup id="cite_ref-nemirowski_10-0" class="reference"><a href="#cite_note-nemirowski-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Lewis_basic" class="mw-redirect" title="Lewis basic">Lewis-basic</a> nitrogen, oxygen, sulphur, or halide <a href="/wiki/Substituent" title="Substituent">substituents</a> bonded to the divalent carbon can <a href="/wiki/Ylide" title="Ylide">delocalize an electron pair into an empty <i>p</i> orbital</a> to stabilize the singlet state. This phenomenon underlies <a href="/wiki/Persistent_carbene" title="Persistent carbene">persistent carbenes</a>' remarkable stability. </p> <div class="mw-heading mw-heading2"><h2 id="Reactivity">Reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbene&action=edit&section=3" title="Edit section: Reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbenes behave like very aggressive <a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis acids</a>. They can attack <a href="/wiki/Lone_pair" title="Lone pair">lone pairs</a>, but their primary synthetic utility arises from attacks on <a href="/wiki/Pi_bond" title="Pi bond">π bonds</a>, which give cyclopropanes; and on <a href="/wiki/Sigma_bond" title="Sigma bond">σ bonds</a>, which cause <a href="/wiki/Carbene_C%E2%88%92H_insertion" title="Carbene C−H insertion">carbene insertion</a>. Other reactions include rearrangements and dimerizations. A particular carbene's reactivity depends on the <a href="/wiki/Substituent" title="Substituent">substituents</a>, including any <a href="/wiki/Metal" title="Metal">metals</a> present. </p> <div class="mw-heading mw-heading3"><h3 id="Singlet-triplet_effects">Singlet-triplet effects</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbene&action=edit&section=4" title="Edit section: Singlet-triplet effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Frame"><a href="/wiki/File:Singlettriplet.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Singlettriplet.svg/512px-Singlettriplet.svg.png" decoding="async" width="512" height="162" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Singlettriplet.svg/768px-Singlettriplet.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Singlettriplet.svg/1024px-Singlettriplet.svg.png 2x" data-file-width="512" data-file-height="162" /></a><figcaption>Carbene addition to alkenes</figcaption></figure> <p>Singlet and triplet carbenes exhibit divergent reactivity.<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><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (January 2024)">page needed</span></a></i>]</sup><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><p>Triplet carbenes are <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">diradicals</a>, and participate in stepwise <a href="/wiki/Single_electron_transfer" class="mw-redirect" title="Single electron transfer">radical additions</a>. Triplet carbene addition necessarily involves (at least one) <a href="/wiki/Reactive_intermediate" title="Reactive intermediate">intermediate</a> with two unpaired electrons. </p><p>Singlet carbenes can (and do) react as <a href="/wiki/Electrophile" title="Electrophile">electrophiles</a>, <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a>, or <a href="/w/index.php?title=Ambiphile_(chemistry)&action=edit&redlink=1" class="new" title="Ambiphile (chemistry) (page does not exist)">ambiphiles</a>.<sup id="cite_ref-FOOTNOTEGrossman200335_4-1" class="reference"><a href="#cite_note-FOOTNOTEGrossman200335-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Their reactions are typically <a href="/wiki/Concerted_reaction" title="Concerted reaction">concerted</a> and often <a href="/wiki/Cheletropic_reaction" title="Cheletropic reaction">cheletropic</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2024)">citation needed</span></a></i>]</sup> Singlet carbenes are typically electrophilic,<sup id="cite_ref-FOOTNOTEGrossman200335_4-2" class="reference"><a href="#cite_note-FOOTNOTEGrossman200335-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> unless they have a filled <i>p</i> orbital, in which case they can react as Lewis bases. The <a href="/wiki/Bamford%E2%80%93Stevens_reaction" title="Bamford–Stevens reaction">Bamford–Stevens reaction</a> gives carbenes in <a href="/wiki/Aprotic_solvent" class="mw-redirect" title="Aprotic solvent">aprotic solvents</a> and <a href="/wiki/Carbenium_ion" title="Carbenium ion">carbenium ions</a> in <a href="/wiki/Protic_solvent" title="Protic solvent">protic ones</a>. </p><p>The different mechanisms imply that singlet carbene additions are <a href="/wiki/Stereospecific" class="mw-redirect" title="Stereospecific">stereospecific</a> but triplet carbene additions <a href="/wiki/Stereoselective" class="mw-redirect" title="Stereoselective">stereoselective</a>. Methylene from <a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a> <a href="/wiki/Photolysis" class="mw-redirect" title="Photolysis">photolysis</a> reacts with either <i>cis</i>- or <i>trans</i>-<a href="/wiki/2-butene" class="mw-redirect" title="2-butene">2-butene</a> to give a single <a href="/wiki/Diastereomer" title="Diastereomer">diastereomer</a> of <a href="/wiki/1,2-Dimethylcyclopropane" title="1,2-Dimethylcyclopropane">1,2-dimethylcyclopropane</a>: <i>cis</i> from <i>cis</i> and <i>trans</i> from <i>trans</i>. Thus methylene is a singlet carbene; if it were triplet, the product would not depend on the starting alkene geometry.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Cyclopropanation">Cyclopropanation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbene&action=edit&section=5" title="Edit section: Cyclopropanation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cyclopropanation" title="Cyclopropanation">Cyclopropanation</a></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Cyclopropanation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Cyclopropanation.svg/220px-Cyclopropanation.svg.png" decoding="async" width="220" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Cyclopropanation.svg/330px-Cyclopropanation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/Cyclopropanation.svg/440px-Cyclopropanation.svg.png 2x" data-file-width="1435" data-file-height="295" /></a><figcaption>Carbene cyclopropanation</figcaption></figure> <p>Carbenes add to double bonds to form <a href="/wiki/Cyclopropane#Cyclopropanes" title="Cyclopropane">cyclopropanes</a>,<sup id="cite_ref-FOOTNOTEGrossman200385–86_14-0" class="reference"><a href="#cite_note-FOOTNOTEGrossman200385–86-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> and, in the presence of a copper <a href="/wiki/Catalysis" title="Catalysis">catalyst</a>, to <a href="/wiki/Alkyne" title="Alkyne">alkynes</a> to give <a href="/wiki/Cyclopropene#Syntheses_of_derivatives" title="Cyclopropene">cyclopropenes</a>. Addition reactions are commonly very fast and <a href="/wiki/Exothermic" class="mw-redirect" title="Exothermic">exothermic</a>, and carbene generation limits reaction rate. </p><p>In <a href="/wiki/Simmons%E2%80%93Smith_reaction" title="Simmons–Smith reaction">Simmons-Smith cyclopropanation</a>, the <a href="/wiki/Iodomethylzinc_iodide" title="Iodomethylzinc iodide">iodomethylzinc iodide</a> typically complexes to any <a href="/wiki/Allyl_alcohol" title="Allyl alcohol">allylic hydroxy groups</a> such that addition is <a href="/wiki/Syn_addition" class="mw-redirect" title="Syn addition"><i>syn</i></a> to the <a href="/wiki/Hydroxy_group" title="Hydroxy group">hydroxy group</a>. </p> <div class="mw-heading mw-heading3"><h3 id="C—H_insertion"><span id="C.E2.80.94H_insertion"></span>C—H insertion</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbene&action=edit&section=6" title="Edit section: C—H insertion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Carbene_C%E2%88%92H_insertion" title="Carbene C−H insertion">Carbene C−H insertion</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Carbene_one-step-insertion.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Carbene_one-step-insertion.svg/220px-Carbene_one-step-insertion.svg.png" decoding="async" width="220" height="46" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Carbene_one-step-insertion.svg/330px-Carbene_one-step-insertion.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Carbene_one-step-insertion.svg/440px-Carbene_one-step-insertion.svg.png 2x" data-file-width="512" data-file-height="108" /></a><figcaption>Carbene insertion</figcaption></figure> <p><a href="/wiki/Carbene_C-H_insertion" class="mw-redirect" title="Carbene C-H insertion">Insertions</a> are another common type of carbene reaction,<sup id="cite_ref-FOOTNOTEGrossman200386–87_15-0" class="reference"><a href="#cite_note-FOOTNOTEGrossman200386–87-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> a form of <a href="/wiki/Oxidative_addition" title="Oxidative addition">oxidative addition</a>. Insertions may or may not occur in single step (see above). The end result is that the carbene interposes itself into an existing bond, preferably X–H (X not carbon), else C–H or (failing that) a C–C bond. <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> carbenes insert much more selectively than methylene, which does not differentiate between primary, secondary, and tertiary C-H bonds. </p> <figure class="mw-halign-left" typeof="mw:File/Frame"><a href="/wiki/File:Carbene_intra.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Carbene_intra.svg/512px-Carbene_intra.svg.png" decoding="async" width="512" height="182" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Carbene_intra.svg/768px-Carbene_intra.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Carbene_intra.svg/1024px-Carbene_intra.svg.png 2x" data-file-width="512" data-file-height="182" /></a><figcaption>Carbene intramolecular reaction</figcaption></figure> <figure class="mw-halign-left" typeof="mw:File/Frame"><a href="/wiki/File:Carbene_intermolecular_insertion.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Carbene_intermolecular_insertion.svg/512px-Carbene_intermolecular_insertion.svg.png" decoding="async" width="512" height="66" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Carbene_intermolecular_insertion.svg/768px-Carbene_intermolecular_insertion.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Carbene_intermolecular_insertion.svg/1024px-Carbene_intermolecular_insertion.svg.png 2x" data-file-width="512" data-file-height="66" /></a><figcaption>Carbene intermolecular reaction</figcaption></figure> <p>The <a href="/wiki/1,2-rearrangement" title="1,2-rearrangement">1,2-rearrangement</a> produced from intramolecular insertion into a bond adjacent to the carbene center is a nuisance in some reaction schemes, as it consumes the carbene to yield the same effect as a traditional <a href="/wiki/Elimination_reaction" title="Elimination reaction">elimination reaction</a>.<sup id="cite_ref-FOOTNOTEGrossman200387_16-0" class="reference"><a href="#cite_note-FOOTNOTEGrossman200387-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Generally, rigid structures favor <a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">intramolecular</a> insertions. In flexible structures, five-membered ring formation is preferred to six-membered ring formation. When such insertions are possible, no <a href="/wiki/Intermolecular" class="mw-redirect" title="Intermolecular">intermolecular</a> insertions are seen. Both inter- and intra-molecular insertions admit asymmetric induction from a chiral metal catalyst. </p> <div class="mw-heading mw-heading3"><h3 id="Electrophilic_attack">Electrophilic attack</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbene&action=edit&section=7" title="Edit section: Electrophilic attack"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbenes can form adducts with nucleophiles, and are a common precursor to various <a href="/wiki/1,3-dipole" title="1,3-dipole">1,3-dipoles</a>.<sup id="cite_ref-FOOTNOTEGrossman200387_16-1" class="reference"><a href="#cite_note-FOOTNOTEGrossman200387-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Carbene_dimerization">Carbene dimerization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbene&action=edit&section=8" title="Edit section: Carbene dimerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Carbene_dimerization" title="Carbene dimerization">Carbene dimerization</a></div> <figure class="mw-halign-right" typeof="mw:File/Frame"><a href="/wiki/File:Wanzlick_equilibrium_lemal_Hahn_1999.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Wanzlick_equilibrium_lemal_Hahn_1999.svg/401px-Wanzlick_equilibrium_lemal_Hahn_1999.svg.png" decoding="async" width="401" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Wanzlick_equilibrium_lemal_Hahn_1999.svg/602px-Wanzlick_equilibrium_lemal_Hahn_1999.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/Wanzlick_equilibrium_lemal_Hahn_1999.svg/802px-Wanzlick_equilibrium_lemal_Hahn_1999.svg.png 2x" data-file-width="401" data-file-height="131" /></a><figcaption>Wanzlick equilibrium</figcaption></figure> <p>Carbenes and <a href="/wiki/Carbenoid" title="Carbenoid">carbenoid</a> precursors can <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimerize</a> to <a href="/wiki/Alkene" title="Alkene">alkenes</a>. This is often, but not always, an unwanted side reaction; metal carbene dimerization has been used in the synthesis of polyalkynylethenes and is the major industrial route to Teflon (see <a href="#Industrial_applications">Carbene § Industrial applications</a>). Persistent carbenes equilibrate with their respective dimers, the <a href="/wiki/Wanzlick_equilibrium" title="Wanzlick equilibrium">Wanzlick equilibrium</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Ligands_in_organometallic_chemistry">Ligands in organometallic chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbene&action=edit&section=9" title="Edit section: Ligands in organometallic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic</a> species, metal complexes with the formulae L<sub>n</sub>MCRR' are often described as carbene complexes.<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> Such species do not however react like free carbenes and are rarely generated from carbene precursors, except for the persistent carbenes.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="See subsequent cite arguing otherwise (January 2024)">citation needed</span></a></i>]</sup><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> The <a href="/wiki/Transition_metal_carbene_complex" title="Transition metal carbene complex">transition metal carbene complexes</a> can be classified according to their reactivity, with the first two classes being the most clearly defined: </p> <ul><li><a href="/wiki/Fischer_carbene" title="Fischer carbene">Fischer carbenes</a>, in which the carbene is bonded to a metal that bears an electron-withdrawing group (usually a carbonyl). In such cases the carbenoid carbon is mildly electrophilic.</li> <li><a href="/wiki/Schrock_carbene" class="mw-redirect" title="Schrock carbene">Schrock carbenes</a>, in which the carbene is bonded to a metal that bears an electron-donating group. In such cases the carbenoid carbon is nucleophilic and resembles a Wittig reagent (which are not considered carbene derivatives).</li> <li><a href="/wiki/Carbene_radical" title="Carbene radical">Carbene radicals</a>, in which the carbene is bonded to an open-shell metal with the carbene carbon possessing a radical character. Carbene radicals have features of both Fischer and Schrock carbenes, but are typically long-lived reaction intermediates.</li> <li><figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Grubbs_catalyst_Gen2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Grubbs_catalyst_Gen2.svg/220px-Grubbs_catalyst_Gen2.svg.png" decoding="async" width="220" height="143" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Grubbs_catalyst_Gen2.svg/330px-Grubbs_catalyst_Gen2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Grubbs_catalyst_Gen2.svg/440px-Grubbs_catalyst_Gen2.svg.png 2x" data-file-width="512" data-file-height="332" /></a><figcaption>The "second generation" of the <a href="/wiki/Grubbs_catalyst" title="Grubbs catalyst">Grubbs catalysts</a> for <a href="/wiki/Alkene_metathesis" class="mw-redirect" title="Alkene metathesis">alkene metathesis</a> features an NHC ligand.</figcaption></figure><a href="/wiki/Persistent_carbene" title="Persistent carbene">N-Heterocyclic</a> (NHC), <a href="/wiki/Anthony_Joseph_Arduengo_III" class="mw-redirect" title="Anthony Joseph Arduengo III">Arduengo</a> or <a href="/wiki/Wanzlick_equilibrium" title="Wanzlick equilibrium">Wanzlick</a> carbenes<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> are C-deprotonated imidazolium or dihydroimidazolium salts. They often are deployed as <a href="/wiki/Ligand" title="Ligand">ancillary ligands</a> in <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>. Such carbenes are usually very strong σ-donor <a href="/wiki/Spectator_ligand" title="Spectator ligand">spectator ligands</a>, similar to phosphines.<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><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></li></ul> <div class="mw-heading mw-heading2"><h2 id="Industrial_applications">Industrial applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbene&action=edit&section=10" title="Edit section: Industrial applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A large-scale application of carbenes is the industrial production of <a href="/wiki/Tetrafluoroethylene" title="Tetrafluoroethylene">tetrafluoroethylene</a>, the precursor to <a href="/wiki/Teflon" class="mw-redirect" title="Teflon">Teflon</a>. Tetrafluoroethylene is generated via the intermediacy of <a href="/wiki/Difluorocarbene" title="Difluorocarbene">difluorocarbene</a>:<sup id="cite_ref-William_22-0" class="reference"><a href="#cite_note-William-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>CHClF<sub>2</sub> → CF<sub>2</sub> + HCl</dd> <dd>2 CF<sub>2</sub> → F<sub>2</sub>C=CF<sub>2</sub></dd></dl> <p>The insertion of carbenes into C–H bonds has been exploited widely, e.g. the <a href="/wiki/Surface_functionalization" class="mw-redirect" title="Surface functionalization">functionalization</a> of polymeric materials<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> and electro-curing of <a href="/wiki/Adhesive" title="Adhesive">adhesives</a>.<sup id="cite_ref-:1_24-0" class="reference"><a href="#cite_note-:1-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Many applications rely on synthetic 3-aryl-3-trifluoromethyl<a href="/wiki/Diazirine" title="Diazirine">diazirines</a><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_26-0" class="reference"><a href="#cite_note-:0-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> (a carbene precursor that can be activated by heat,<sup id="cite_ref-:2_27-0" class="reference"><a href="#cite_note-:2-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> light,<sup id="cite_ref-:0_26-1" class="reference"><a href="#cite_note-:0-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:2_27-1" class="reference"><a href="#cite_note-:2-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Voltage" title="Voltage">voltage</a>)<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_24-1" class="reference"><a href="#cite_note-:1-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> but there is a whole family of <a href="/wiki/Carbene_dye" title="Carbene dye">carbene dyes</a>. </p> <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=Carbene&action=edit&section=11" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbenes had first been postulated by <a href="/wiki/Eduard_Buchner" title="Eduard Buchner">Eduard Buchner</a> in 1903 in <a href="/wiki/Cyclopropanation" title="Cyclopropanation">cyclopropanation</a> studies of <a href="/wiki/Ethyl_diazoacetate" title="Ethyl diazoacetate">ethyl diazoacetate</a> with toluene.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> In 1912 <a href="/wiki/Hermann_Staudinger" title="Hermann Staudinger">Hermann Staudinger</a><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> also converted alkenes to cyclopropanes with <a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a> and CH<sub>2</sub> as an intermediate. <a href="/wiki/William_von_Eggers_Doering" title="William von Eggers Doering">Doering</a> in 1954 demonstrated their synthetic utility with <a href="/wiki/Dichlorocarbene" title="Dichlorocarbene">dichlorocarbene</a>.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbene&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/Transition_metal_carbene_complex" title="Transition metal carbene complex">Transition metal carbene complexes</a></li> <li><a href="/wiki/Atomic_carbon" title="Atomic carbon">Atomic carbon</a> a single carbon atom with the chemical formula :C:, in effect a twofold carbene. Also has been used to make "true carbenes" in situ.</li> <li><a href="/wiki/Foiled_carbene" title="Foiled carbene">Foiled carbenes</a> derive their stability from proximity of a double bond (i.e. their ability to form conjugated systems).</li> <li><a href="/wiki/Carbene_analogs" class="mw-redirect" title="Carbene analogs">Carbene analogs</a> and <a href="/wiki/Carbenoids" class="mw-redirect" title="Carbenoids">carbenoids</a></li> <li><a href="/wiki/Carbenium_ion" title="Carbenium ion">Carbenium ions</a>, protonated carbenes</li> <li><a href="/wiki/Ring_opening_metathesis_polymerization" class="mw-redirect" title="Ring opening metathesis polymerization">Ring opening metathesis polymerization</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=Carbene&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 reflist-columns references-column-width" style="column-width: 33em;"> <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 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 id="CITEREFHoffmann2005" class="citation book cs1"><a href="/wiki/Roald_Hoffmann" title="Roald Hoffmann">Hoffmann, Roald</a> (2005). <i>Molecular Orbitals of Transition Metal Complexes</i>. Oxford. p. 7. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-853093-0" title="Special:BookSources/978-0-19-853093-0"><bdi>978-0-19-853093-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Molecular+Orbitals+of+Transition+Metal+Complexes&rft.pages=7&rft.pub=Oxford&rft.date=2005&rft.isbn=978-0-19-853093-0&rft.aulast=Hoffmann&rft.aufirst=Roald&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbene" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/C00806.html">carbenes</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.C00806">10.1351/goldbook.C00806</a></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGrossman2003" class="citation book cs1">Grossman, Robert B. (2003). <i>The Art of Writing Reasonable Organic Reaction Mechanisms</i> (2nd ed.). New York: Springer. p. 84. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-387-95468-6" title="Special:BookSources/0-387-95468-6"><bdi>0-387-95468-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Art+of+Writing+Reasonable+Organic+Reaction+Mechanisms&rft.place=New+York&rft.pages=84&rft.edition=2nd&rft.pub=Springer&rft.date=2003&rft.isbn=0-387-95468-6&rft.aulast=Grossman&rft.aufirst=Robert+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbene" class="Z3988"></span></span> </li> <li id="cite_note-FOOTNOTEGrossman200335-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-FOOTNOTEGrossman200335_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FOOTNOTEGrossman200335_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-FOOTNOTEGrossman200335_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a href="#CITEREFGrossman2003">Grossman 2003</a>, p. 35.</span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text">For detailed reviews on stable carbenes, see: (a) <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBourissouGuerretGabbaiBertrand2000" class="citation journal cs1">Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. (2000). "Stable Carbenes". <i><a href="/wiki/Chem._Rev." class="mw-redirect" title="Chem. Rev.">Chem. Rev.</a></i> <b>100</b> (1): 39–91. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr940472u">10.1021/cr940472u</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11749234">11749234</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Rev.&rft.atitle=Stable+Carbenes&rft.volume=100&rft.issue=1&rft.pages=39-91&rft.date=2000&rft_id=info%3Adoi%2F10.1021%2Fcr940472u&rft_id=info%3Apmid%2F11749234&rft.aulast=Bourissou&rft.aufirst=D.&rft.au=Guerret%2C+O.&rft.au=Gabbai%2C+F.+P.&rft.au=Bertrand%2C+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbene" class="Z3988"></span> (b) <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMelaimiSoleilhavoupBertrand2010" class="citation journal cs1">Melaimi, M.; Soleilhavoup, M.; Bertrand, G. (2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3130005">"Stable cyclic carbenes and related species beyond diaminocarbenes"</a>. <i><a href="/wiki/Angew._Chem._Int._Ed." class="mw-redirect" title="Angew. Chem. Int. Ed.">Angew. Chem. Int. Ed.</a></i> <b>49</b> (47): 8810–8849. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.201000165">10.1002/anie.201000165</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3130005">3130005</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20836099">20836099</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.&rft.atitle=Stable+cyclic+carbenes+and+related+species+beyond+diaminocarbenes&rft.volume=49&rft.issue=47&rft.pages=8810-8849&rft.date=2010&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3130005%23id-name%3DPMC&rft_id=info%3Apmid%2F20836099&rft_id=info%3Adoi%2F10.1002%2Fanie.201000165&rft.aulast=Melaimi&rft.aufirst=M.&rft.au=Soleilhavoup%2C+M.&rft.au=Bertrand%2C+G.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3130005&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbene" class="Z3988"></span></span> </li> <li id="cite_note-FOOTNOTEGrossman200384–85-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-FOOTNOTEGrossman200384–85_6-0">^</a></b></span> <span class="reference-text"><a href="#CITEREFGrossman2003">Grossman 2003</a>, pp. 84–85.</span> </li> <li id="cite_note-FOOTNOTEGrossman200385-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-FOOTNOTEGrossman200385_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FOOTNOTEGrossman200385_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a href="#CITEREFGrossman2003">Grossman 2003</a>, p. 85.</span> </li> <li id="cite_note-FOOTNOTEGrossman200384-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-FOOTNOTEGrossman200384_8-0">^</a></b></span> <span class="reference-text"><a href="#CITEREFGrossman2003">Grossman 2003</a>, p. 84.</span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGrasseBrauerZupancicKaufmann1983" class="citation journal cs1">Grasse, P. B.; Brauer, B. E.; Zupancic, J. J.; Kaufmann, K. J.; Schuster, G. B. (1983). "Chemical and physical properties of fluorenylidene: equilibration of the singlet and triplet carbenes". <i>Journal of the American Chemical Society</i>. <b>105</b> (23): 6833. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00361a014">10.1021/ja00361a014</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Chemical+and+physical+properties+of+fluorenylidene%3A+equilibration+of+the+singlet+and+triplet+carbenes&rft.volume=105&rft.issue=23&rft.pages=6833&rft.date=1983&rft_id=info%3Adoi%2F10.1021%2Fja00361a014&rft.aulast=Grasse&rft.aufirst=P.+B.&rft.au=Brauer%2C+B.+E.&rft.au=Zupancic%2C+J.+J.&rft.au=Kaufmann%2C+K.+J.&rft.au=Schuster%2C+G.+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbene" class="Z3988"></span></span> </li> <li id="cite_note-nemirowski-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-nemirowski_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNemirowski,_A.Schreiner,_P._R.2007" class="citation journal cs1">Nemirowski, A.; Schreiner, P. R. (November 2007). "Electronic Stabilization of Ground State Triplet Carbenes". <i>J. Org. Chem</i>. <b>72</b> (25): 9533–9540. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo701615x">10.1021/jo701615x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17994760">17994760</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Org.+Chem.&rft.atitle=Electronic+Stabilization+of+Ground+State+Triplet+Carbenes&rft.volume=72&rft.issue=25&rft.pages=9533-9540&rft.date=2007-11&rft_id=info%3Adoi%2F10.1021%2Fjo701615x&rft_id=info%3Apmid%2F17994760&rft.au=Nemirowski%2C+A.&rft.au=Schreiner%2C+P.+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbene" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmith,_Michael_B.March,_Jerry2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.au=Smith%2C+Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbene" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text">Contrariwise, <a href="#CITEREFGrossman2003">Grossman 2003</a>, p. 85 states: "The reactivities of carbenes and carbenoids are the same no matter how they are generated." Grossman's analysis is not supported by modern physical organic chemistry texts, and likely refers to rapid equilibration between carbene states following most carbene generation methods.</span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSkellWoodworth1956" class="citation journal cs1">Skell, P. S.; Woodworth, R. C. (1956). "Structure of Carbene, Ch2". <i>Journal of the American Chemical Society</i>. <b>78</b> (17): 4496. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01598a087">10.1021/ja01598a087</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Structure+of+Carbene%2C+Ch2&rft.volume=78&rft.issue=17&rft.pages=4496&rft.date=1956&rft_id=info%3Adoi%2F10.1021%2Fja01598a087&rft.aulast=Skell&rft.aufirst=P.+S.&rft.au=Woodworth%2C+R.+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbene" class="Z3988"></span></span> </li> <li id="cite_note-FOOTNOTEGrossman200385–86-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-FOOTNOTEGrossman200385–86_14-0">^</a></b></span> <span class="reference-text"><a href="#CITEREFGrossman2003">Grossman 2003</a>, pp. 85–86.</span> </li> <li id="cite_note-FOOTNOTEGrossman200386–87-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-FOOTNOTEGrossman200386–87_15-0">^</a></b></span> <span class="reference-text"><a href="#CITEREFGrossman2003">Grossman 2003</a>, pp. 86–87.</span> </li> <li id="cite_note-FOOTNOTEGrossman200387-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-FOOTNOTEGrossman200387_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FOOTNOTEGrossman200387_16-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a href="#CITEREFGrossman2003">Grossman 2003</a>, p. 87.</span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text">For a concise tutorial on the applications of carbene ligands also beyond diaminocarbenes, see <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMunz2018" class="citation journal cs1">Munz, D (2018). "Pushing Electrons—Which Carbene Ligand for Which Application?". <i><a href="/wiki/Organometallics" title="Organometallics">Organometallics</a></i>. <b>37</b> (3): 275–289. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.organomet.7b00720">10.1021/acs.organomet.7b00720</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organometallics&rft.atitle=Pushing+Electrons%E2%80%94Which+Carbene+Ligand+for+Which+Application%3F&rft.volume=37&rft.issue=3&rft.pages=275-289&rft.date=2018&rft_id=info%3Adoi%2F10.1021%2Facs.organomet.7b00720&rft.aulast=Munz&rft.aufirst=D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbene" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text">Contrariwise, <a href="#CITEREFGrossman2003">Grossman 2003</a>: "Diazo compounds are converted to singlet carbenes upon gentle warming and to carbenoids by treatment with a Rh(II) or Cu(II) salt such as Rh<sub>2</sub>(OAc)<sub>4</sub> or CuCl<sub>2</sub>. The transition-metal-derived carbenoids, which have a metal –– C double bond, undergo the reactions typical of singlet carbenes. At this point you can think of them as free singlet carbenes, even though they’re not."</span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text">For a general review with a focus on applications with diaminocarbenes, see: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHopkinsonRichterSchedlerGlorius2014" class="citation journal cs1">Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. (2014). "An overview of N-heterocyclic carbenes". <i><a href="/wiki/Nature_(journal)" title="Nature (journal)">Nature</a></i>. <b>510</b> (7506): 485–496. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2014Natur.510..485H">2014Natur.510..485H</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnature13384">10.1038/nature13384</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24965649">24965649</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:672379">672379</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=An+overview+of+N-heterocyclic+carbenes&rft.volume=510&rft.issue=7506&rft.pages=485-496&rft.date=2014&rft_id=info%3Adoi%2F10.1038%2Fnature13384&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A672379%23id-name%3DS2CID&rft_id=info%3Apmid%2F24965649&rft_id=info%3Abibcode%2F2014Natur.510..485H&rft.aulast=Hopkinson&rft.aufirst=M.+N.&rft.au=Richter%2C+C.&rft.au=Schedler%2C+M.&rft.au=Glorius%2C+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbene" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text">S. P. Nolan "N-Heterocyclic Carbenes in Synthesis" 2006, Wiley-VCH, Weinheim. Print <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527314003" title="Special:BookSources/9783527314003">9783527314003</a>. Online <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527609451" title="Special:BookSources/9783527609451">9783527609451</a>. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9783527609451">10.1002/9783527609451</a></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarionDiez-GonzalezNolan2007" class="citation journal cs1">Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. (2007). "N-heterocyclic carbenes as organocatalysts". <i>Angew. Chem. Int. Ed</i>. <b>46</b> (17): 2988–3000. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.200603380">10.1002/anie.200603380</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17348057">17348057</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.&rft.atitle=N-heterocyclic+carbenes+as+organocatalysts&rft.volume=46&rft.issue=17&rft.pages=2988-3000&rft.date=2007&rft_id=info%3Adoi%2F10.1002%2Fanie.200603380&rft_id=info%3Apmid%2F17348057&rft.aulast=Marion&rft.aufirst=N.&rft.au=Diez-Gonzalez%2C+S.&rft.au=Nolan%2C+S.+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbene" class="Z3988"></span></span> </li> <li id="cite_note-William-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-William_22-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBajzer2004" class="citation book cs1">Bajzer, W. 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style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a class="mw-selflink selflink">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" 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:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" 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:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" 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