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href="#Reaction_mechanism"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Reaction mechanism</span> </div> </a> <ul id="toc-Reaction_mechanism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Modifications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Modifications"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Modifications</span> </div> </a> <button aria-controls="toc-Modifications-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 Modifications subsection</span> </button> <ul id="toc-Modifications-sublist" class="vector-toc-list"> <li id="toc-Photochemical_rearrangement" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Photochemical_rearrangement"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Photochemical rearrangement</span> </div> </a> <ul id="toc-Photochemical_rearrangement-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Variations" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Variations"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Variations</span> </div> </a> <button aria-controls="toc-Variations-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 Variations subsection</span> </button> <ul id="toc-Variations-sublist" class="vector-toc-list"> <li id="toc-Darapsky_degradation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Darapsky_degradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Darapsky degradation</span> </div> </a> <ul id="toc-Darapsky_degradation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Harger_reaction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Harger_reaction"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Harger reaction</span> </div> </a> <ul id="toc-Harger_reaction-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthetic_applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthetic_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Synthetic applications</span> </div> </a> <button aria-controls="toc-Synthetic_applications-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 Synthetic applications subsection</span> </button> <ul 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id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> 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class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Curtius rearrangement</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 16 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-16" 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">16 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D8%B9%D8%A7%D8%AF%D8%A9_%D8%AA%D8%B1%D8%AA%D9%8A%D8%A8_%D9%83%D9%88%D8%B1%D8%AA%D9%8A%D9%88%D8%B3" title="إعادة ترتيب كورتيوس – Arabic" lang="ar" hreflang="ar" data-title="إعادة ترتيب كورتيوس" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Transposici%C3%B3_de_Curtius" title="Transposició de Curtius – Catalan" lang="ca" hreflang="ca" data-title="Transposició de Curtius" 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/Curti%C5%AFv_p%C5%99esmyk" title="Curtiův přesmyk – Czech" lang="cs" hreflang="cs" data-title="Curtiův přesmyk" 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/Curtius-Reaktion" title="Curtius-Reaktion – German" lang="de" hreflang="de" data-title="Curtius-Reaktion" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Transposici%C3%B3n_de_Curtius" title="Transposición de Curtius – Spanish" lang="es" hreflang="es" data-title="Transposición de Curtius" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A8%D8%A7%D8%B2%D8%A2%D8%B1%D8%A7%DB%8C%DB%8C_%DA%A9%D9%88%D8%B1%D8%AA%DB%8C%D9%88%D8%B3" title="بازآرایی کورتیوس – Persian" lang="fa" hreflang="fa" data-title="بازآرایی کورتیوس" 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/R%C3%A9arrangement_de_Curtius" title="Réarrangement de Curtius – French" lang="fr" hreflang="fr" data-title="Réarrangement de Curtius" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Riarrangiamento_di_Curtius" title="Riarrangiamento di Curtius – Italian" lang="it" hreflang="it" data-title="Riarrangiamento di Curtius" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Curtius-lebont%C3%A1s" title="Curtius-lebontás – Hungarian" lang="hu" hreflang="hu" data-title="Curtius-lebontás" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Curtius-omlegging" title="Curtius-omlegging – Dutch" lang="nl" hreflang="nl" data-title="Curtius-omlegging" 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%AF%E3%83%AB%E3%83%81%E3%82%A6%E3%82%B9%E8%BB%A2%E4%BD%8D" title="クルチウス転位 – Japanese" lang="ja" hreflang="ja" data-title="クルチウス転位" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Przegrupowanie_Curtiusa" title="Przegrupowanie Curtiusa – Polish" lang="pl" hreflang="pl" data-title="Przegrupowanie Curtiusa" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Transpozi%C8%9Bie_Curtius" title="Transpoziție Curtius – Romanian" lang="ro" hreflang="ro" data-title="Transpoziție Curtius" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Curtius-toisiintuminen" title="Curtius-toisiintuminen – Finnish" lang="fi" hreflang="fi" data-title="Curtius-toisiintuminen" 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 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<div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical reaction</div> <style data-mw-deduplicate="TemplateStyles:r1049416944">.mw-parser-output .ib-reactionbox{border-collapse:collapse}.mw-parser-output .ib-reactionbox td,.mw-parser-output .ib-reactionbox th{border:1px solid #a2a9b1}</style> <table class="infobox ib-reactionbox"> <tbody><tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Curtius rearrangement </th></tr> <tr> <td>Named after </td> <td><a href="/wiki/Theodor_Curtius" title="Theodor Curtius">Theodor Curtius</a> </td></tr> <tr> <td>Reaction type </td> <td><a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">Rearrangement reaction</a> </td></tr> <tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Identifiers </th></tr> <tr> <td>Organic Chemistry Portal </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://www.organic-chemistry.org/namedreactions/curtius-rearrangement.shtm">curtius-rearrangement</a></span> </td></tr> <tr> <td><a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">RSC</a> ontology ID </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/ols/ontologies/rxno/terms?iri=http%3A%2F%2Fpurl.obolibrary.org%2Fobo%2FRXNO_0000054">RXNO:0000054</a></span> </td></tr> <tr> <td style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2"> </td></tr> </tbody></table> <p>The <b>Curtius rearrangement</b> (or <b>Curtius reaction</b> or <b>Curtius degradation</b>), first defined by <a href="/wiki/Theodor_Curtius" title="Theodor Curtius">Theodor Curtius</a> in 1885, is the <a href="/wiki/Thermal_decomposition" title="Thermal decomposition">thermal decomposition</a> of an <a href="/wiki/Acyl_azide" title="Acyl azide">acyl azide</a> to an <a href="/wiki/Isocyanate" title="Isocyanate">isocyanate</a> with loss of <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> gas.<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> The isocyanate then undergoes attack by a variety of <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a> such as water, <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> and <a href="/wiki/Amine" title="Amine">amines</a>, to yield a primary amine, <a href="/wiki/Carbamate" title="Carbamate">carbamate</a> or <a href="/wiki/Urea" title="Urea">urea derivative</a> respectively.<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> Several reviews have been published.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Curtius_rearrangement_rxn.png" class="mw-file-description" title="Summary scheme of the Curtius rearrangement"><img alt="Summary scheme of the Curtius rearrangement" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Curtius_rearrangement_rxn.png/600px-Curtius_rearrangement_rxn.png" decoding="async" width="600" height="284" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Curtius_rearrangement_rxn.png/900px-Curtius_rearrangement_rxn.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Curtius_rearrangement_rxn.png/1200px-Curtius_rearrangement_rxn.png 2x" data-file-width="1643" data-file-height="779" /></a><figcaption>Summary scheme of the Curtius rearrangement</figcaption></figure> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Preparation_of_acyl_azide">Preparation of acyl azide</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=1" title="Edit section: Preparation of acyl azide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:DPPA-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/DPPA-3D-balls.png/180px-DPPA-3D-balls.png" decoding="async" width="180" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/DPPA-3D-balls.png/270px-DPPA-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/DPPA-3D-balls.png/360px-DPPA-3D-balls.png 2x" data-file-width="1055" data-file-height="1100" /></a><figcaption><a href="/wiki/Diphenylphosphoryl_azide" title="Diphenylphosphoryl azide">Diphenylphosphoryl azide</a></figcaption></figure> <p>The acyl azide is usually made from the reaction of <a href="/wiki/Acid_chloride" class="mw-redirect" title="Acid chloride">acid chlorides</a> or <a href="/wiki/Organic_acid_anhydride" title="Organic acid anhydride">anhydrides</a><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> with <a href="/wiki/Sodium_azide" title="Sodium azide">sodium azide</a><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Trimethylsilyl_azide" title="Trimethylsilyl azide">trimethylsilyl azide</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Acyl azides are also obtained from treating <a href="/wiki/Acylhydrazine" class="mw-redirect" title="Acylhydrazine">acylhydrazines</a> with <a href="/wiki/Nitrous_acid" title="Nitrous acid">nitrous acid</a>.<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> Alternatively, the acyl azide can be formed by the direct reaction of a carboxylic acid with <a href="/wiki/Diphenylphosphoryl_azide" title="Diphenylphosphoryl azide">diphenylphosphoryl azide</a> (DPPA).<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acyl_azide_formation.png" class="mw-file-description" title="Methods of forming acyl azides from carboxylic acids"><img alt="Methods of forming acyl azides from carboxylic acids" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Acyl_azide_formation.png/400px-Acyl_azide_formation.png" decoding="async" width="400" height="226" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Acyl_azide_formation.png/600px-Acyl_azide_formation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/02/Acyl_azide_formation.png/800px-Acyl_azide_formation.png 2x" data-file-width="1386" data-file-height="784" /></a><figcaption>Methods of forming acyl azides from carboxylic acids</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Reaction_mechanism">Reaction mechanism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=2" title="Edit section: Reaction mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It was believed that the Curtius rearrangement was a two-step processes, with the loss of nitrogen gas forming an <a href="/wiki/Acyl_nitrene" class="mw-redirect" title="Acyl nitrene">acyl nitrene</a>, followed by migration of the R-group to give the <a href="/wiki/Isocyanate" title="Isocyanate">isocyanate</a>. However, recent research has indicated that the thermal decomposition is a <a href="/wiki/Concerted_reaction" title="Concerted reaction">concerted process</a>,<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> with both steps happening together, due to the absence of any nitrene insertion or addition byproducts observed or isolated in the reaction.<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> Thermodynamic calculations also support a concerted mechanism.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Curtius_rearrangement_mech_concerted.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Curtius_rearrangement_mech_concerted.png/500px-Curtius_rearrangement_mech_concerted.png" decoding="async" width="500" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Curtius_rearrangement_mech_concerted.png/750px-Curtius_rearrangement_mech_concerted.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Curtius_rearrangement_mech_concerted.png/1000px-Curtius_rearrangement_mech_concerted.png 2x" data-file-width="1451" data-file-height="336" /></a><figcaption>Mechanism of the Curtius rearrangement</figcaption></figure> <p>The migration occurs with full retention of configuration at the R-group. The <a href="/wiki/Migratory_aptitude" title="Migratory aptitude">migratory aptitude</a> of the R-group is roughly tertiary > secondary ~ aryl > primary. The isocyanate formed can then be <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a> to give a primary <a href="/wiki/Amine" title="Amine">amine</a>, or undergo <a href="/wiki/Nucleophile" title="Nucleophile">nucleophilic attack</a> with <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> and amines to form <a href="/wiki/Carbamate" title="Carbamate">carbamates</a> and <a href="/wiki/Urea" title="Urea">urea derivatives</a> respectively. </p> <div class="mw-heading mw-heading2"><h2 id="Modifications">Modifications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=3" title="Edit section: Modifications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Research has shown that the Curtius rearrangement is <a href="/wiki/Catalysis" title="Catalysis">catalyzed</a> by both <a href="/wiki/Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Brønsted</a><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Lewis_acids" class="mw-redirect" title="Lewis acids">Lewis acids</a>, via the protonation of, or coordination to the acyl oxygen atom respectively. For example, Fahr and Neumann have shown that the use of <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">boron trifluoride</a> or <a href="/wiki/Boron_trichloride" title="Boron trichloride">boron trichloride</a> catalyst reduces the decomposition temperature needed for rearrangement by about 100 °C, and increases the yield of the isocyanate significantly.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Photochemical_rearrangement">Photochemical rearrangement</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=4" title="Edit section: Photochemical rearrangement"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Curtius_rearrangement_photochemical_mech.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Curtius_rearrangement_photochemical_mech.png/525px-Curtius_rearrangement_photochemical_mech.png" decoding="async" width="525" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Curtius_rearrangement_photochemical_mech.png/788px-Curtius_rearrangement_photochemical_mech.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/61/Curtius_rearrangement_photochemical_mech.png/1050px-Curtius_rearrangement_photochemical_mech.png 2x" data-file-width="1872" data-file-height="336" /></a><figcaption>Mechanism of the photochemical Curtius rearrangement</figcaption></figure> <p><a href="/wiki/Photochemistry" title="Photochemistry">Photochemical</a> decomposition of the acyl azide is also possible.<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> However, photochemical rearrangement is not concerted and instead occurs by a <a href="/wiki/Nitrene" title="Nitrene">nitrene</a> intermediate, formed by the cleavage of the weak N–N bond and the loss of nitrogen gas. The highly reactive nitrene can undergo a variety of nitrene reactions, such as <a href="/wiki/Nitrene#Reactions" title="Nitrene">nitrene insertion</a> and addition, giving unwanted side products.<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> In the example below, the nitrene intermediate inserts into one of the C–H bonds of the <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> solvent to form N-cyclohexylbenzamide as a side product. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Curtius_rearrangement_nitrene_insertion.png" class="mw-file-description" title="Insertion of nitrene formed by photochemical Curtius rearrangement"><img alt="Insertion of nitrene formed by photochemical Curtius rearrangement" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Curtius_rearrangement_nitrene_insertion.png/450px-Curtius_rearrangement_nitrene_insertion.png" decoding="async" width="450" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Curtius_rearrangement_nitrene_insertion.png/675px-Curtius_rearrangement_nitrene_insertion.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Curtius_rearrangement_nitrene_insertion.png/900px-Curtius_rearrangement_nitrene_insertion.png 2x" data-file-width="1338" data-file-height="304" /></a><figcaption>Insertion of nitrene formed by photochemical Curtius rearrangement</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Variations">Variations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=5" title="Edit section: Variations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Darapsky_degradation">Darapsky degradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=6" title="Edit section: Darapsky degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In one variation called the <b>Darapsky degradation</b>,<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> or <b>Darapsky synthesis</b>, a Curtius rearrangement takes place as one of the steps in the conversion of an α-cyanoester to an <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a>. <a href="/wiki/Hydrazine" title="Hydrazine">Hydrazine</a> is used to convert the ester to an <a href="/wiki/Acylhydrazine" class="mw-redirect" title="Acylhydrazine">acylhydrazine</a>, which is reacted with <a href="/wiki/Nitrous_acid" title="Nitrous acid">nitrous acid</a> to give the acyl azide. Heating the azide in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> yields the <a href="/wiki/Ethyl_carbamate" title="Ethyl carbamate">ethyl carbamate</a> via the Curtius rearrangement. Acid hydrolysis yields the amine from the carbamate and the carboxylic acid from the nitrile simultaneously, giving the product amino acid.<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> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Darapsky_amino_acid_synthesis.png" class="mw-file-description" title="Scheme of the Darapsky amino acid synthesis"><img alt="Scheme of the Darapsky amino acid synthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Darapsky_amino_acid_synthesis.png/800px-Darapsky_amino_acid_synthesis.png" decoding="async" width="800" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Darapsky_amino_acid_synthesis.png/1200px-Darapsky_amino_acid_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Darapsky_amino_acid_synthesis.png/1600px-Darapsky_amino_acid_synthesis.png 2x" data-file-width="2719" data-file-height="482" /></a><figcaption>Scheme of the Darapsky amino acid synthesis</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Harger_reaction">Harger reaction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=7" title="Edit section: Harger reaction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The photochemical Curtius-like migration and rearrangement of a phosphinic azide forms a metaphosphonimidate<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> in what is also known as the <b>Harger reaction</b> (named after Dr Martin Harger from <a href="/wiki/University_of_Leicester" title="University of Leicester">University of Leicester</a>).<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> This is followed by hydrolysis, in the example below with <a href="/wiki/Methanol" title="Methanol">methanol</a>, to give a phosphonamidate. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Harger_reaction_scheme.png" class="mw-file-description" title="Scheme of the Harger reaction"><img alt="Scheme of the Harger reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Harger_reaction_scheme.png/550px-Harger_reaction_scheme.png" decoding="async" width="550" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Harger_reaction_scheme.png/825px-Harger_reaction_scheme.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Harger_reaction_scheme.png/1100px-Harger_reaction_scheme.png 2x" data-file-width="1383" data-file-height="263" /></a><figcaption>Scheme of the Harger reaction</figcaption></figure> <p>Unlike the Curtius rearrangement, there is a choice of R-groups on the phosphinic azide which can migrate. Harger has found that the alkyl groups migrate preferentially to aryl groups, and this preference increases in the order methyl < primary < secondary < tertiary. This is probably due to steric and conformational factors, as the bulkier the R-group, the less favorable the conformation for phenyl migration.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthetic_applications">Synthetic applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=8" title="Edit section: Synthetic applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Curtius rearrangement is tolerant of a large variety of <a href="/wiki/Functional_group" title="Functional group">functional groups</a>, and has significant synthetic utility, as many different groups can be incorporated depending on the choice of <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a> used to attack the isocyanate. </p><p>For example, when carried out in the presence of <a href="/wiki/Tert-Butanol" class="mw-redirect" title="Tert-Butanol"><i>tert</i>-butanol</a>, the reaction generates <a href="/wiki/Tert-butyloxycarbonyl_protecting_group" class="mw-redirect" title="Tert-butyloxycarbonyl protecting group">Boc</a>-<a href="/wiki/Protecting_group" title="Protecting group">protected</a> amines, useful intermediates in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><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> Likewise, when the Curtius reaction is performed in the presence of <a href="/wiki/Benzyl_alcohol" title="Benzyl alcohol">benzyl alcohol</a>, <a href="/wiki/Carboxybenzyl" class="mw-redirect" title="Carboxybenzyl">Cbz</a>-protected amines are formed.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Triquinacene">Triquinacene</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=9" title="Edit section: Triquinacene"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/R._B._Woodward" class="mw-redirect" title="R. B. Woodward">R. B. Woodward</a> et al. used the Curtius rearrangement as one of the steps in the <a href="/wiki/Total_synthesis" title="Total synthesis">total synthesis</a> of the <a href="/wiki/Polyquinane" title="Polyquinane">polyquinane</a> triquinacene in 1964. Following hydrolysis of the ester in the intermediate (<b>1</b>), a Curtius rearrangement was effected to convert the carboxylic acid groups in (<b>2</b>) to the <a href="/wiki/Methyl_carbamate" title="Methyl carbamate">methyl carbamate</a> groups (<b>3</b>) with 84% yield. Further steps then gave triquinacene (<b>4</b>).<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Woodward_triquinacene_curtius_rearr.png" class="mw-file-description" title="The Curtius reaction in Woodward's total synthesis of triquinacene"><img alt="The Curtius reaction in Woodward's total synthesis of triquinacene" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Woodward_triquinacene_curtius_rearr.png/600px-Woodward_triquinacene_curtius_rearr.png" decoding="async" width="600" height="139" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Woodward_triquinacene_curtius_rearr.png/900px-Woodward_triquinacene_curtius_rearr.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Woodward_triquinacene_curtius_rearr.png/1200px-Woodward_triquinacene_curtius_rearr.png 2x" data-file-width="2173" data-file-height="502" /></a><figcaption>The Curtius reaction in Woodward's total synthesis of triquinacene</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Oseltamivir">Oseltamivir</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=10" title="Edit section: Oseltamivir"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In their synthesis of the <a href="/wiki/Antiviral" class="mw-redirect" title="Antiviral">antiviral</a> drug <a href="/wiki/Oseltamivir" title="Oseltamivir">oseltamivir</a>, also known as Tamiflu, Ishikawa et al. used the Curtius rearrangement in one of the key steps in converting the acyl azide to the <a href="/wiki/Amide_group" class="mw-redirect" title="Amide group">amide group</a> in the target molecule. In this case, the isocyanate formed by the rearrangement is attacked by a carboxylic acid to form the amide. Subsequent reactions could all be carried out in the same reaction vessel to give the final product with 57% overall yield. An important benefit of the Curtius reaction highlighted by the authors was that it could be carried out at room temperature, minimizing the hazard from heating. The scheme overall was highly efficient, requiring only three “one-pot” operations to produce this important and valuable drug used for the treatment of <a href="/wiki/Avian_influenza" title="Avian influenza">avian influenza</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> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ishikawa_oseltaimvir_curtius_rearr.png" class="mw-file-description" title="The Curtius rearrangement in the Ishikawa total synthesis of oseltamivir"><img alt="The Curtius rearrangement in the Ishikawa total synthesis of oseltamivir" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Ishikawa_oseltaimvir_curtius_rearr.png/750px-Ishikawa_oseltaimvir_curtius_rearr.png" decoding="async" width="750" height="183" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Ishikawa_oseltaimvir_curtius_rearr.png/1125px-Ishikawa_oseltaimvir_curtius_rearr.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Ishikawa_oseltaimvir_curtius_rearr.png/1500px-Ishikawa_oseltaimvir_curtius_rearr.png 2x" data-file-width="2397" data-file-height="586" /></a><figcaption>The Curtius rearrangement in the Ishikawa total synthesis of oseltamivir</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Dievodiamine">Dievodiamine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=11" title="Edit section: Dievodiamine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Dievodiamine is a <a href="/wiki/Natural_product" title="Natural product">natural product</a> from the plant <i><a href="/wiki/Euodia_ruticarpa" class="mw-redirect" title="Euodia ruticarpa">Euodia ruticarpa</a></i>, which is widely used in <a href="/wiki/Traditional_Chinese_medicine" title="Traditional Chinese medicine">traditional Chinese medicine</a>. Unsworth et al.’s <a href="/wiki/Protecting_group" title="Protecting group">protecting group</a>-free total synthesis of dievodiamine utilizes the Curtius rearrangement in the first step of the synthesis, catalyzed by <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">boron trifluoride</a>. The activated isocyanate then quickly reacts with the <a href="/wiki/Indole" title="Indole">indole</a> ring in an <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitution</a> reaction to give the amide in 94% yield, and subsequent steps give dievodamine.<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> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Dievodiamine_curtius_rearr.png" class="mw-file-description" title="The Curtius rearrangement in the total synthesis of Dievodiamine"><img alt="The Curtius rearrangement in the total synthesis of Dievodiamine" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/51/Dievodiamine_curtius_rearr.png/910px-Dievodiamine_curtius_rearr.png" decoding="async" width="910" height="192" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/51/Dievodiamine_curtius_rearr.png/1365px-Dievodiamine_curtius_rearr.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/51/Dievodiamine_curtius_rearr.png/1820px-Dievodiamine_curtius_rearr.png 2x" data-file-width="3016" data-file-height="635" /></a><figcaption>The Curtius rearrangement in the total synthesis of Dievodiamine</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&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/Beckmann_rearrangement" title="Beckmann rearrangement">Beckmann rearrangement</a></li> <li><a href="/wiki/Bergmann_degradation" title="Bergmann degradation">Bergmann degradation</a></li> <li><a href="/wiki/Hofmann_rearrangement" title="Hofmann rearrangement">Hofmann rearrangement</a></li> <li><a href="/wiki/Lossen_rearrangement" title="Lossen rearrangement">Lossen rearrangement</a></li> <li><a href="/wiki/Schmidt_reaction" title="Schmidt reaction">Schmidt reaction</a></li> <li><a href="/wiki/Tiemann_rearrangement" class="mw-redirect" title="Tiemann rearrangement">Tiemann rearrangement</a></li> <li><a href="/wiki/Neber_rearrangement" title="Neber rearrangement">Neber rearrangement</a></li> <li><a href="/wiki/Wolff_rearrangement" title="Wolff rearrangement">Wolff rearrangement</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=Curtius_rearrangement&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 reflist-columns-2"> <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="CITEREFCurtius,_Th.1890" class="citation journal cs1">Curtius, Th. (1890). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k90721q/f915.image.langEN">"Ueber Stickstoffwasserstoffsäure (Azoimid) N<sub>3</sub>H"</a> [On hydrazoic acid (azoimide) N<sub>3</sub>H]. <i>Berichte der Deutschen Chemischen Gesellschaft zu Berlin</i>. <b>23</b> (2): 3023–3033. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.189002302232">10.1002/cber.189002302232</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft+zu+Berlin&rft.atitle=Ueber+Stickstoffwasserstoffs%C3%A4ure+%28Azoimid%29+N%3Csub%3E3%3C%2Fsub%3EH&rft.volume=23&rft.issue=2&rft.pages=3023-3033&rft.date=1890&rft_id=info%3Adoi%2F10.1002%2Fcber.189002302232&rft.au=Curtius%2C+Th.&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k90721q%2Ff915.image.langEN&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCurtius1894" class="citation journal cs1">Curtius, T. (1894). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1427976">"20. Hydrazide und Azide organischer Säuren I. Abhandlung"</a> [Hydrazides and azides of organic acids I. paper]. <i>Journal für Praktische Chemie</i>. <b>50</b>: 275–294. <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%2Fprac.18940500125">10.1002/prac.18940500125</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+f%C3%BCr+Praktische+Chemie&rft.atitle=20.+Hydrazide+und+Azide+organischer+S%C3%A4uren+I.+Abhandlung&rft.volume=50&rft.pages=275-294&rft.date=1894&rft_id=info%3Adoi%2F10.1002%2Fprac.18940500125&rft.aulast=Curtius&rft.aufirst=T.&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1427976&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></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="CITEREFKaiser,_C.Weinstock,_J.1988" class="citation journal cs1">Kaiser, C.; Weinstock, J. (1988). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv6p0910">"Amines from mixed carboxylic-carbonic anhydrides: 1-phenylcyclopentylamine"</a>. <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Amines+from+mixed+carboxylic-carbonic+anhydrides%3A+1-phenylcyclopentylamine&rft.date=1988&rft.au=Kaiser%2C+C.&rft.au=Weinstock%2C+J.&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3Dcv6p0910&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><i>Collected Volumes</i>, vol. 6, p. 910</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=910&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span>.</span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmith,_P._A._S.1946" class="citation journal cs1">Smith, P. A. S. (1946). "The Curtius reaction". <i><a href="/wiki/Organic_Reactions" title="Organic Reactions">Organic Reactions</a></i>. <b>3</b>: 337–449.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Reactions&rft.atitle=The+Curtius+reaction&rft.volume=3&rft.pages=337-449&rft.date=1946&rft.au=Smith%2C+P.+A.+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScrivenTurnbull1988" class="citation journal cs1">Scriven, Eric F. V.; Turnbull, Kenneth (1988). "Azides: their preparation and synthetic uses". <i>Chemical Reviews</i>. <b>88</b> (2): 297–368. <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%2Fcr00084a001">10.1021/cr00084a001</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=Azides%3A+their+preparation+and+synthetic+uses&rft.volume=88&rft.issue=2&rft.pages=297-368&rft.date=1988&rft_id=info%3Adoi%2F10.1021%2Fcr00084a001&rft.aulast=Scriven&rft.aufirst=Eric+F.+V.&rft.au=Turnbull%2C+Kenneth&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeinstock1961" class="citation journal cs1">Weinstock, J (1961). "Modified Curtius reaction". <i>J. Org. Chem</i>. <b>26</b>: 3511. <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%2Fjo01067a604">10.1021/jo01067a604</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=Modified+Curtius+reaction&rft.volume=26&rft.pages=3511&rft.date=1961&rft_id=info%3Adoi%2F10.1021%2Fjo01067a604&rft.aulast=Weinstock&rft.aufirst=J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="Carey" class="citation book cs1">Carey, Francis A.; Sundberg, Richard J. (2007). <i>Advanced Organic Chemistry: Part B: Reactions and Synthesis</i> (5th ed.). New York: Springer. p. 948. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0387683546" title="Special:BookSources/978-0387683546"><bdi>978-0387683546</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+Part+B%3A+Reactions+and+Synthesis&rft.place=New+York&rft.pages=948&rft.edition=5th&rft.pub=Springer&rft.date=2007&rft.isbn=978-0387683546&rft.au=Carey%2C+Francis+A.&rft.au=Sundberg%2C+Richard+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWarrenPress1980" class="citation journal cs1">Warren, J. D.; Press, J. B. (1980). "Formation and Curtius rearrangement of acyl azides from unreactive acid chlorides". <i>Synth. Commun</i>. <b>10</b>: 107–110. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F00397918008061812">10.1080/00397918008061812</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Synth.+Commun.&rft.atitle=Formation+and+Curtius+rearrangement+of+acyl+azides+from+unreactive+acid+chlorides&rft.volume=10&rft.pages=107-110&rft.date=1980&rft_id=info%3Adoi%2F10.1080%2F00397918008061812&rft.aulast=Warren&rft.aufirst=J.+D.&rft.au=Press%2C+J.+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></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="CITEREFPozsgayJennings1987" class="citation journal cs1">Pozsgay, V.; Jennings, H. J. (1987). "Azide synthesis with stable nitrosyl salts". <i>Tetrahedron Lett</i>. <b>28</b> (43): 5091–5092. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0040-4039%2800%2995598-9">10.1016/s0040-4039(00)95598-9</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Lett.&rft.atitle=Azide+synthesis+with+stable+nitrosyl+salts&rft.volume=28&rft.issue=43&rft.pages=5091-5092&rft.date=1987&rft_id=info%3Adoi%2F10.1016%2Fs0040-4039%2800%2995598-9&rft.aulast=Pozsgay&rft.aufirst=V.&rft.au=Jennings%2C+H.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShioiriNinomiyaYamada1972" class="citation journal cs1">Shioiri, T.; Ninomiya, K.; Yamada, S. (1972). "New convenient reagent for a modified Curtius reaction and for peptide synthesis". <i>J. Am. Chem. Soc</i>. <b>94</b> (17): 6203–6205. <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%2Fja00772a052">10.1021/ja00772a052</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/5054412">5054412</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=New+convenient+reagent+for+a+modified+Curtius+reaction+and+for+peptide+synthesis&rft.volume=94&rft.issue=17&rft.pages=6203-6205&rft.date=1972&rft_id=info%3Adoi%2F10.1021%2Fja00772a052&rft_id=info%3Apmid%2F5054412&rft.aulast=Shioiri&rft.aufirst=T.&rft.au=Ninomiya%2C+K.&rft.au=Yamada%2C+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" 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="Carey" class="citation book cs1">Carey, Francis A.; Sundberg, Richard J. (2007). <i>Advanced Organic Chemistry: Part B: Reactions and Synthesis</i> (5th ed.). New York: Springer. p. 948. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0387683546" title="Special:BookSources/978-0387683546"><bdi>978-0387683546</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+Part+B%3A+Reactions+and+Synthesis&rft.place=New+York&rft.pages=948&rft.edition=5th&rft.pub=Springer&rft.date=2007&rft.isbn=978-0387683546&rft.au=Carey%2C+Francis+A.&rft.au=Sundberg%2C+Richard+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="Carey" class="citation book cs1">Carey, Francis A.; Sundberg, Richard J. (2007). <i>Advanced Organic Chemistry: Part B: Reactions and Synthesis</i> (5th ed.). New York: Springer. p. 948. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0387683546" title="Special:BookSources/978-0387683546"><bdi>978-0387683546</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+Part+B%3A+Reactions+and+Synthesis&rft.place=New+York&rft.pages=948&rft.edition=5th&rft.pub=Springer&rft.date=2007&rft.isbn=978-0387683546&rft.au=Carey%2C+Francis+A.&rft.au=Sundberg%2C+Richard+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></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="CITEREFRaukAlewood1977" class="citation journal cs1">Rauk, A.; Alewood, P. F. (1977). "A theoretical study of the Curtius rearrangement. The electronic structures and interconversion of the CHNO species". <i>Can. J. Chem</i>. <b>55</b> (9): 1498–1510. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fv77-209">10.1139/v77-209</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Can.+J.+Chem.&rft.atitle=A+theoretical+study+of+the+Curtius+rearrangement.+The+electronic+structures+and+interconversion+of+the+CHNO+species.&rft.volume=55&rft.issue=9&rft.pages=1498-1510&rft.date=1977&rft_id=info%3Adoi%2F10.1139%2Fv77-209&rft.aulast=Rauk&rft.aufirst=A.&rft.au=Alewood%2C+P.+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFL'Abbe1969" class="citation journal cs1">L'Abbe, G. (1969). "Decomposition and addition reactions of organic azides". <i>Chem. Rev</i>. <b>69</b> (3): 345–363. <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%2Fcr60259a004">10.1021/cr60259a004</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=Decomposition+and+addition+reactions+of+organic+azides&rft.volume=69&rft.issue=3&rft.pages=345-363&rft.date=1969&rft_id=info%3Adoi%2F10.1021%2Fcr60259a004&rft.aulast=L%27Abbe&rft.aufirst=G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYukawaTsuno1959" class="citation journal cs1">Yukawa, Y.; Tsuno, Y. (1959). "The decomposition of substituted benzazides in acidic solvents, the acid catalysis". <i>J. Am. Chem. Soc</i>. <b>81</b>: 2007–2012. <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%2Fja01517a055">10.1021/ja01517a055</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=The+decomposition+of+substituted+benzazides+in+acidic+solvents%2C+the+acid+catalysis&rft.volume=81&rft.pages=2007-2012&rft.date=1959&rft_id=info%3Adoi%2F10.1021%2Fja01517a055&rft.aulast=Yukawa&rft.aufirst=Y.&rft.au=Tsuno%2C+Y.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFahrNeumann1965" class="citation journal cs1">Fahr, E.; Neumann, L. (1965). "Curtius-Reaktion mit Bortrihalogeniden". <i>Angew. Chem</i>. <b>77</b> (13): 591. <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/1965AngCh..77..591F">1965AngCh..77..591F</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fange.19650771308">10.1002/ange.19650771308</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.&rft.atitle=Curtius-Reaktion+mit+Bortrihalogeniden&rft.volume=77&rft.issue=13&rft.pages=591&rft.date=1965&rft_id=info%3Adoi%2F10.1002%2Fange.19650771308&rft_id=info%3Abibcode%2F1965AngCh..77..591F&rft.aulast=Fahr&rft.aufirst=E.&rft.au=Neumann%2C+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWentrupBornemann2005" class="citation journal cs1">Wentrup, C.; Bornemann, H. (2005). "Curtius rearrangment of acyl azides revisited - formation of cyanate". <i>Eur. J. Org. Chem.</i>: 4521–4524. <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%2Fejoc.200500545">10.1002/ejoc.200500545</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Eur.+J.+Org.+Chem.&rft.atitle=Curtius+rearrangment+of+acyl+azides+revisited+-+formation+of+cyanate&rft.pages=4521-4524&rft.date=2005&rft_id=info%3Adoi%2F10.1002%2Fejoc.200500545&rft.aulast=Wentrup&rft.aufirst=C.&rft.au=Bornemann%2C+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEiblerSauer1974" class="citation journal cs1">Eibler, E.; Sauer, J. (1974). "Ein Betrag zur Isocyanatbildung bei der Photolyse von Acylaziden". <i>Tetrahedron Lett</i>. <b>15</b> (30): 2569–2572. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0040-4039%2801%2992295-6">10.1016/s0040-4039(01)92295-6</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Lett.&rft.atitle=Ein+Betrag+zur+Isocyanatbildung+bei+der+Photolyse+von+Acylaziden&rft.volume=15&rft.issue=30&rft.pages=2569-2572&rft.date=1974&rft_id=info%3Adoi%2F10.1016%2Fs0040-4039%2801%2992295-6&rft.aulast=Eibler&rft.aufirst=E.&rft.au=Sauer%2C+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></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">August Darapsky (1936) "Darstellung von α-Aminosäuren aus Alkyl-cyanessigsäuren" (Preparation of α-amino acids from alkyl cyanoacetic acids), <i>Journal für Praktische Chemie</i>, <b>146</b> : 250-267.</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGagnonBovinCraig1951" class="citation journal cs1">Gagnon, P. E.; Bovin, P. A.; Craig, H. M. (1951). <a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fcjc-29-1-70">"Synthesis of amino acids from substituted cyanoacetic esters"</a>. <i>Can. J. Chem</i>. <b>29</b>: 70–75. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fcjc-29-1-70">10.1139/cjc-29-1-70</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Can.+J.+Chem.&rft.atitle=Synthesis+of+amino+acids+from+substituted+cyanoacetic+esters&rft.volume=29&rft.pages=70-75&rft.date=1951&rft_id=info%3Adoi%2F10.1139%2Fcjc-29-1-70&rft.aulast=Gagnon&rft.aufirst=P.+E.&rft.au=Bovin%2C+P.+A.&rft.au=Craig%2C+H.+M.&rft_id=https%3A%2F%2Fdoi.org%2F10.1139%252Fcjc-29-1-70&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></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="CITEREFBertrandMajoralBaceiredo1980" class="citation journal cs1">Bertrand, G.; Majoral, J.; Baceiredo, A. (1980). "Photolytic rearrangement of phosphorus azide: evidence for a transient metaphosphonimidate". <i>Tetrahedron Lett</i>. <b>21</b> (52): 5015–5018. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0040-4039%2800%2971119-1">10.1016/s0040-4039(00)71119-1</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Lett.&rft.atitle=Photolytic+rearrangement+of+phosphorus+azide%3A+evidence+for+a+transient+metaphosphonimidate&rft.volume=21&rft.issue=52&rft.pages=5015-5018&rft.date=1980&rft_id=info%3Adoi%2F10.1016%2Fs0040-4039%2800%2971119-1&rft.aulast=Bertrand&rft.aufirst=G.&rft.au=Majoral%2C+J.&rft.au=Baceiredo%2C+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHargerWestlake1982" class="citation journal cs1">Harger, M. J. P.; Westlake, S. (1982). "Photolysis of some unsymmetrical phosphinic azides in methanol". <i>Tetrahedron</i>. <b>38</b> (20): 3073–3078. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0040-4020%2882%2980195-6">10.1016/0040-4020(82)80195-6</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Photolysis+of+some+unsymmetrical+phosphinic+azides+in+methanol&rft.volume=38&rft.issue=20&rft.pages=3073-3078&rft.date=1982&rft_id=info%3Adoi%2F10.1016%2F0040-4020%2882%2980195-6&rft.aulast=Harger&rft.aufirst=M.+J.+P.&rft.au=Westlake%2C+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHargerWestlake1982" class="citation journal cs1">Harger, M. J. P.; Westlake, S. (1982). "Photolysis of some unsymmetrical phosphinic azides in methanol". <i>Tetrahedron</i>. <b>38</b> (20): 3073–3078. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0040-4020%2882%2980195-6">10.1016/0040-4020(82)80195-6</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Photolysis+of+some+unsymmetrical+phosphinic+azides+in+methanol&rft.volume=38&rft.issue=20&rft.pages=3073-3078&rft.date=1982&rft_id=info%3Adoi%2F10.1016%2F0040-4020%2882%2980195-6&rft.aulast=Harger&rft.aufirst=M.+J.+P.&rft.au=Westlake%2C+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAm_EndeDevriesCliffordBrenek1998" class="citation journal cs1">Am Ende, David J.; Devries, Keith M.; Clifford, Pamela J.; Brenek, Steven J. (1998). "A Calorimetric Investigation to Safely Scale-Up a Curtius Rearrangement of Acryloyl Azide". <i>Organic Process Research & Development</i>. <b>2</b> (6): 382–392. <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%2Fop970115w">10.1021/op970115w</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Process+Research+%26+Development&rft.atitle=A+Calorimetric+Investigation+to+Safely+Scale-Up+a+Curtius+Rearrangement+of+Acryloyl+Azide&rft.volume=2&rft.issue=6&rft.pages=382-392&rft.date=1998&rft_id=info%3Adoi%2F10.1021%2Fop970115w&rft.aulast=Am+Ende&rft.aufirst=David+J.&rft.au=Devries%2C+Keith+M.&rft.au=Clifford%2C+Pamela+J.&rft.au=Brenek%2C+Steven+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLebelLeogane2005" class="citation journal cs1">Lebel, H.; Leogane, O. (2005). "Boc-protected amines via a mild and efficient one-pot Curtius rearrangement". <i>Organic Letters</i>. <b>7</b> (19): 4107–4110. <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%2Fol051428b">10.1021/ol051428b</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/16146363">16146363</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Letters&rft.atitle=Boc-protected+amines+via+a+mild+and+efficient+one-pot+Curtius+rearrangement&rft.volume=7&rft.issue=19&rft.pages=4107-4110&rft.date=2005&rft_id=info%3Adoi%2F10.1021%2Fol051428b&rft_id=info%3Apmid%2F16146363&rft.aulast=Lebel&rft.aufirst=H.&rft.au=Leogane%2C+O.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJessup,_P._J.Petty,_C._B.Roos,_J.Overman,_L._E.1988" class="citation journal cs1">Jessup, P. J.; Petty, C. B.; Roos, J.; Overman, L. E. (1988). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv6p0095">"1-<i>N</i>-Acylamino-1,3-dienes from 2,4-pentadienoic acids by the Curtius rearrangement: benzyl <i>trans</i>-1,3-butadiene-1-carbamate"</a>. <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=1-N-Acylamino-1%2C3-dienes+from+2%2C4-pentadienoic+acids+by+the+Curtius+rearrangement%3A+benzyl+trans-1%2C3-butadiene-1-carbamate&rft.date=1988&rft.au=Jessup%2C+P.+J.&rft.au=Petty%2C+C.+B.&rft.au=Roos%2C+J.&rft.au=Overman%2C+L.+E.&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3Dcv6p0095&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><i>Collected Volumes</i>, vol. 6, p. 95</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=95&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span>.</span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWoodwardFukunagaKelly1964" class="citation journal cs1">Woodward, R. B.; Fukunaga, T.; Kelly, R. C. (1964). "Triquinacene". <i>J. Am. Chem. Soc</i>. <b>86</b> (15): 3162–3164. <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%2Fja01069a046">10.1021/ja01069a046</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Triquinacene&rft.volume=86&rft.issue=15&rft.pages=3162-3164&rft.date=1964&rft_id=info%3Adoi%2F10.1021%2Fja01069a046&rft.aulast=Woodward&rft.aufirst=R.+B.&rft.au=Fukunaga%2C+T.&rft.au=Kelly%2C+R.+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIshikawaSuzukiHayashi2009" class="citation journal cs1">Ishikawa, H.; Suzuki, T.; Hayashi, Y. (2009). "High-yielding synthesis of the anti-influenza neuramidase inhibitor (-)-oseltamivir by three "one-pot" operations". <i>Angew. Chem. Int. Ed</i>. <b>48</b> (7): 1304–1307. <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.200804883">10.1002/anie.200804883</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/19123206">19123206</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=High-yielding+synthesis+of+the+anti-influenza+neuramidase+inhibitor+%28-%29-oseltamivir+by+three+%22one-pot%22+operations&rft.volume=48&rft.issue=7&rft.pages=1304-1307&rft.date=2009&rft_id=info%3Adoi%2F10.1002%2Fanie.200804883&rft_id=info%3Apmid%2F19123206&rft.aulast=Ishikawa&rft.aufirst=H.&rft.au=Suzuki%2C+T.&rft.au=Hayashi%2C+Y.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFUnsworthKitsiouTaylor2013" class="citation journal cs1">Unsworth, William P.; Kitsiou, Christiana; Taylor, Richard J. K. (5 July 2013). "An Expedient Protecting-Group-Free Total Synthesis of (±)-Dievodiamine". <i>Organic Letters</i>. <b>15</b> (13): 3302–3305. <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%2Fol4013469">10.1021/ol4013469</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/23786450">23786450</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Letters&rft.atitle=An+Expedient+Protecting-Group-Free+Total+Synthesis+of+%28%C2%B1%29-Dievodiamine&rft.volume=15&rft.issue=13&rft.pages=3302-3305&rft.date=2013-07-05&rft_id=info%3Adoi%2F10.1021%2Fol4013469&rft_id=info%3Apmid%2F23786450&rft.aulast=Unsworth&rft.aufirst=William+P.&rft.au=Kitsiou%2C+Christiana&rft.au=Taylor%2C+Richard+J.+K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACurtius+rearrangement" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Curtius_rearrangement&action=edit&section=14" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output 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reactions"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Topics_in_organic_reactions" style="font-size:114%;margin:0 4em">Topics in <a href="/wiki/Organic_reaction" title="Organic reaction">organic reactions</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Addition_reaction" title="Addition reaction">Addition reaction</a></li> <li><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reaction</a></li> <li><a href="/wiki/Polymerization" title="Polymerization">Polymerization</a></li> <li><a href="/wiki/Category:Reagents_for_organic_chemistry" title="Category:Reagents for organic chemistry">Reagents</a></li> <li><a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">Rearrangement reaction</a></li> <li><a href="/wiki/Organic_redox_reaction" title="Organic redox reaction">Redox reaction</a></li> <li><a href="/wiki/Regioselectivity" title="Regioselectivity">Regioselectivity</a></li> <li><a href="/wiki/Stereoselectivity" title="Stereoselectivity">Stereoselectivity</a></li> <li><a href="/wiki/Stereospecificity" title="Stereospecificity">Stereospecificity</a></li> <li><a href="/wiki/Substitution_reaction" title="Substitution reaction">Substitution reaction</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/A_value" title="A value">A value</a></li> <li><a href="/wiki/Alpha_effect" title="Alpha effect">Alpha effect</a></li> <li><a href="/wiki/Annulene" title="Annulene">Annulene</a></li> <li><a href="/wiki/Anomeric_effect" title="Anomeric effect">Anomeric effect</a></li> <li><a href="/wiki/Antiaromaticity" title="Antiaromaticity">Antiaromaticity</a></li> <li><a href="/wiki/Aromatic_ring_current" title="Aromatic ring current">Aromatic ring current</a></li> <li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a></li> <li><a href="/wiki/Baird%27s_rule" title="Baird's rule">Baird's rule</a></li> <li><a href="/wiki/Baker%E2%80%93Nathan_effect" title="Baker–Nathan effect">Baker–Nathan effect</a></li> <li><a href="/wiki/Baldwin%27s_rules" title="Baldwin's rules">Baldwin's rules</a></li> <li><a href="/wiki/Bema_Hapothle" title="Bema Hapothle">Bema Hapothle</a></li> <li><a href="/wiki/Beta-silicon_effect" class="mw-redirect" title="Beta-silicon effect">Beta-silicon effect</a></li> <li><a href="/wiki/Bicycloaromaticity" title="Bicycloaromaticity">Bicycloaromaticity</a></li> <li><a href="/wiki/Bredt%27s_rule" title="Bredt's rule">Bredt's rule</a></li> <li><a href="/wiki/B%C3%BCrgi%E2%80%93Dunitz_angle" title="Bürgi–Dunitz angle">Bürgi–Dunitz angle</a></li> <li><a href="/wiki/Catalytic_resonance_theory" title="Catalytic resonance theory">Catalytic resonance theory</a></li> <li><a href="/wiki/Charge_remote_fragmentation" class="mw-redirect" title="Charge remote fragmentation">Charge remote fragmentation</a></li> <li><a href="/wiki/Charge-transfer_complex" title="Charge-transfer complex">Charge-transfer complex</a></li> <li><a href="/wiki/Clar%27s_rule" title="Clar's rule">Clar's rule</a></li> <li><a href="/wiki/Conformational_isomerism" title="Conformational isomerism">Conformational isomerism</a></li> <li><a href="/wiki/Conjugated_system" title="Conjugated system">Conjugated system</a></li> <li><a href="/wiki/Conrotatory_and_disrotatory" title="Conrotatory and disrotatory">Conrotatory and disrotatory</a></li> <li><a href="/wiki/Curtin%E2%80%93Hammett_principle" title="Curtin–Hammett principle">Curtin–Hammett principle</a></li> <li><a href="/wiki/Dynamic_binding_(chemistry)" title="Dynamic binding (chemistry)">Dynamic binding (chemistry)</a></li> <li><a href="/wiki/Edwards_equation" title="Edwards equation">Edwards equation</a></li> <li><a href="/wiki/Effective_molarity" title="Effective molarity">Effective molarity</a></li> <li><a href="/wiki/Electromeric_effect" title="Electromeric effect">Electromeric effect</a></li> <li><a href="/wiki/Electron-rich" title="Electron-rich">Electron-rich</a></li> <li><a href="/wiki/Electron-withdrawing_group" title="Electron-withdrawing group">Electron-withdrawing group</a></li> <li><a href="/wiki/Electronic_effect" title="Electronic effect">Electronic effect</a></li> <li><a href="/wiki/Electrophile" title="Electrophile">Electrophile</a></li> <li><a href="/wiki/Evelyn_effect" title="Evelyn effect">Evelyn effect</a></li> <li><a href="/wiki/Flippin%E2%80%93Lodge_angle" title="Flippin–Lodge angle">Flippin–Lodge angle</a></li> <li><a href="/wiki/Free-energy_relationship" title="Free-energy relationship">Free-energy relationship</a></li> <li><a href="/wiki/Grunwald%E2%80%93Winstein_equation" title="Grunwald–Winstein equation">Grunwald–Winstein equation</a></li> <li><a href="/wiki/Hammett_acidity_function" title="Hammett acidity function">Hammett acidity function</a></li> <li><a href="/wiki/Hammett_equation" title="Hammett equation">Hammett equation</a></li> <li><a href="/wiki/George_S._Hammond" title="George S. Hammond">George S. Hammond</a></li> <li><a href="/wiki/Hammond%27s_postulate" title="Hammond's postulate">Hammond's postulate</a></li> <li><a href="/wiki/Homoaromaticity" title="Homoaromaticity">Homoaromaticity</a></li> <li><a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a></li> <li><a href="/wiki/Hyperconjugation" title="Hyperconjugation">Hyperconjugation</a></li> <li><a href="/wiki/Inductive_effect" title="Inductive effect">Inductive effect</a></li> <li><a href="/wiki/Kinetic_isotope_effect" title="Kinetic isotope effect">Kinetic isotope effect</a></li> <li><a href="/wiki/LFER_solvent_coefficients_(data_page)" title="LFER solvent coefficients (data page)">LFER solvent coefficients (data page)</a></li> <li><a href="/wiki/Marcus_theory" title="Marcus theory">Marcus theory</a></li> <li><a href="/wiki/Markovnikov%27s_rule" title="Markovnikov's rule">Markovnikov's rule</a></li> <li><a href="/wiki/M%C3%B6bius_aromaticity" title="Möbius aromaticity">Möbius aromaticity</a></li> <li><a href="/wiki/M%C3%B6bius%E2%80%93H%C3%BCckel_concept" title="Möbius–Hückel concept">Möbius–Hückel concept</a></li> <li><a href="/wiki/More_O%27Ferrall%E2%80%93Jencks_plot" title="More O'Ferrall–Jencks plot">More O'Ferrall–Jencks plot</a></li> <li><a href="/wiki/Negative_hyperconjugation" title="Negative hyperconjugation">Negative hyperconjugation</a></li> <li><a href="/wiki/Neighbouring_group_participation" title="Neighbouring group participation">Neighbouring group participation</a></li> <li><a href="/wiki/2-Norbornyl_cation" title="2-Norbornyl cation">2-Norbornyl cation</a></li> <li><a href="/wiki/Nucleophile" title="Nucleophile">Nucleophile</a></li> <li><a href="/wiki/Kennedy_J._P._Orton" title="Kennedy J. P. Orton">Kennedy J. P. Orton</a></li> <li><a href="/wiki/Passive_binding" title="Passive binding">Passive binding</a></li> <li><a href="/wiki/Phosphaethynolate" title="Phosphaethynolate">Phosphaethynolate</a></li> <li><a href="/wiki/Polar_effect" class="mw-redirect" title="Polar effect">Polar effect</a></li> <li><a href="/wiki/Polyfluorene" title="Polyfluorene">Polyfluorene</a></li> <li><a href="/wiki/Ring_strain" title="Ring strain">Ring strain</a></li> <li><a href="/wiki/%CE%A3-aromaticity" class="mw-redirect" title="Σ-aromaticity">Σ-aromaticity</a></li> <li><a href="/wiki/Spherical_aromaticity" title="Spherical aromaticity">Spherical aromaticity</a></li> <li><a href="/wiki/Spiroaromaticity" class="mw-redirect" title="Spiroaromaticity">Spiroaromaticity</a></li> <li><a href="/wiki/Steric_effects" title="Steric effects">Steric effects</a></li> <li><a href="/wiki/Superaromaticity" class="mw-redirect" title="Superaromaticity">Superaromaticity</a></li> <li><a href="/wiki/Swain%E2%80%93Lupton_equation" title="Swain–Lupton equation">Swain–Lupton equation</a></li> <li><a href="/wiki/Taft_equation" title="Taft equation">Taft equation</a></li> <li><a href="/wiki/Thorpe%E2%80%93Ingold_effect" title="Thorpe–Ingold effect">Thorpe–Ingold effect</a></li> <li><a href="/wiki/Vinylogy" title="Vinylogy">Vinylogy</a></li> <li><a href="/wiki/Walsh_diagram" title="Walsh diagram">Walsh diagram</a></li> <li><a href="/wiki/Woodward%E2%80%93Hoffmann_rules" title="Woodward–Hoffmann rules">Woodward–Hoffmann rules</a></li> <li><a href="/wiki/Woodward%27s_rules" title="Woodward's rules">Woodward's rules</a></li> <li><a href="/wiki/Y-aromaticity" class="mw-redirect" title="Y-aromaticity">Y-aromaticity</a></li> <li><a href="/wiki/Yukawa%E2%80%93Tsuno_equation" title="Yukawa–Tsuno equation">Yukawa–Tsuno equation</a></li> <li><a href="/wiki/Zaitsev%27s_rule" class="mw-redirect" title="Zaitsev's rule">Zaitsev's rule</a></li> <li><a href="/wiki/%CE%A3-bishomoaromaticity" class="mw-redirect" title="Σ-bishomoaromaticity">Σ-bishomoaromaticity</a></li></ul> </div><table class="nowraplinks mw-collapsible autocollapse navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="List_of_organic_reactions" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_organic_reactions" title="List of organic reactions">List of organic reactions</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:7.5em">Carbon-carbon <br /> bond forming <br /> reactions</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetoacetic_ester_synthesis" title="Acetoacetic ester synthesis">Acetoacetic ester synthesis</a></li> <li><a href="/wiki/Acyloin_condensation" title="Acyloin condensation">Acyloin condensation</a></li> <li><a href="/wiki/Aldol_condensation" title="Aldol condensation">Aldol condensation</a></li> <li><a href="/wiki/Aldol_reaction" title="Aldol reaction">Aldol reaction</a></li> <li><a href="/wiki/Alkane_metathesis" title="Alkane metathesis">Alkane metathesis</a></li> <li><a href="/wiki/Alkyne_metathesis" title="Alkyne metathesis">Alkyne metathesis</a></li> <li><a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Alkyne trimerisation</a></li> <li><a href="/wiki/Alkynylation" title="Alkynylation">Alkynylation</a></li> <li><a href="/wiki/Allan%E2%80%93Robinson_reaction" title="Allan–Robinson reaction">Allan–Robinson reaction</a></li> <li><a href="/wiki/Arndt%E2%80%93Eistert_reaction" title="Arndt–Eistert reaction">Arndt–Eistert reaction</a></li> <li><a href="/wiki/Auwers_synthesis" title="Auwers synthesis">Auwers synthesis</a></li> <li><a href="/wiki/Aza-Baylis%E2%80%93Hillman_reaction" title="Aza-Baylis–Hillman reaction">Aza-Baylis–Hillman reaction</a></li> <li><a href="/wiki/Barbier_reaction" title="Barbier reaction">Barbier reaction</a></li> <li><a href="/wiki/Barton%E2%80%93Kellogg_reaction" title="Barton–Kellogg reaction">Barton–Kellogg reaction</a></li> <li><a href="/wiki/Baylis%E2%80%93Hillman_reaction" title="Baylis–Hillman reaction">Baylis–Hillman reaction</a></li> <li><a href="/wiki/Benary_reaction" title="Benary reaction">Benary reaction</a></li> <li><a href="/wiki/Bergman_cyclization" title="Bergman cyclization">Bergman cyclization</a></li> <li><a href="/wiki/Biginelli_reaction" title="Biginelli reaction">Biginelli reaction</a></li> <li><a href="/wiki/Bingel_reaction" title="Bingel reaction">Bingel reaction</a></li> <li><a href="/wiki/Blaise_ketone_synthesis" title="Blaise ketone synthesis">Blaise ketone synthesis</a></li> <li><a href="/wiki/Blaise_reaction" title="Blaise reaction">Blaise reaction</a></li> <li><a href="/wiki/Blanc_chloromethylation" title="Blanc chloromethylation">Blanc chloromethylation</a></li> <li><a href="/wiki/Bodroux%E2%80%93Chichibabin_aldehyde_synthesis" title="Bodroux–Chichibabin aldehyde synthesis">Bodroux–Chichibabin aldehyde synthesis</a></li> <li><a href="/wiki/Bouveault_aldehyde_synthesis" title="Bouveault aldehyde synthesis">Bouveault aldehyde synthesis</a></li> <li><a href="/wiki/Bucherer%E2%80%93Bergs_reaction" title="Bucherer–Bergs reaction">Bucherer–Bergs reaction</a></li> <li><a href="/wiki/Buchner_ring_expansion" title="Buchner ring expansion">Buchner ring expansion</a></li> <li><a href="/wiki/Cadiot%E2%80%93Chodkiewicz_coupling" title="Cadiot–Chodkiewicz coupling">Cadiot–Chodkiewicz coupling</a></li> <li><a href="/wiki/Carbonyl_allylation" title="Carbonyl allylation">Carbonyl allylation</a></li> <li><a href="/wiki/Carbonyl_olefin_metathesis" title="Carbonyl olefin metathesis">Carbonyl olefin metathesis</a></li> <li><a href="/wiki/Castro%E2%80%93Stephens_coupling" title="Castro–Stephens coupling">Castro–Stephens coupling</a></li> <li><a href="/wiki/Chan_rearrangement" title="Chan rearrangement">Chan rearrangement</a></li> <li><a href="/wiki/Chan%E2%80%93Lam_coupling" title="Chan–Lam coupling">Chan–Lam coupling</a></li> <li><a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen condensation</a></li> <li><a href="/wiki/Claisen_rearrangement" title="Claisen rearrangement">Claisen rearrangement</a></li> <li><a href="/wiki/Claisen-Schmidt_condensation" class="mw-redirect" title="Claisen-Schmidt condensation">Claisen-Schmidt condensation</a></li> <li><a href="/wiki/Combes_quinoline_synthesis" title="Combes quinoline synthesis">Combes quinoline synthesis</a></li> <li><a href="/wiki/Corey%E2%80%93Fuchs_reaction" title="Corey–Fuchs reaction">Corey–Fuchs reaction</a></li> <li><a href="/wiki/Corey%E2%80%93House_synthesis" title="Corey–House synthesis">Corey–House synthesis</a></li> <li><a href="/wiki/Coupling_reaction" title="Coupling reaction">Coupling reaction</a></li> <li><a href="/wiki/Cross-coupling_reaction" title="Cross-coupling reaction">Cross-coupling reaction</a></li> <li><a href="/wiki/Cross_dehydrogenative_coupling" title="Cross dehydrogenative coupling">Cross dehydrogenative coupling</a></li> <li><a href="/wiki/Cross-coupling_partner" title="Cross-coupling partner">Cross-coupling partner</a></li> <li><a href="/wiki/Dakin%E2%80%93West_reaction" title="Dakin–West reaction">Dakin–West reaction</a></li> <li><a href="/wiki/Darzens_reaction" title="Darzens reaction">Darzens reaction</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Doebner_reaction" title="Doebner reaction">Doebner reaction</a></li> <li><a href="/wiki/Wulff%E2%80%93D%C3%B6tz_reaction" title="Wulff–Dötz reaction">Wulff–Dötz reaction</a></li> <li><a href="/wiki/Ene_reaction" title="Ene reaction">Ene reaction</a></li> <li><a href="/wiki/Enyne_metathesis" title="Enyne metathesis">Enyne metathesis</a></li> <li><a href="/wiki/Ethenolysis" title="Ethenolysis">Ethenolysis</a></li> <li><a href="/wiki/Favorskii_reaction" title="Favorskii reaction">Favorskii reaction</a></li> <li><a href="/wiki/Ferrier_carbocyclization" title="Ferrier carbocyclization">Ferrier carbocyclization</a></li> <li><a href="/wiki/Friedel%E2%80%93Crafts_reaction" title="Friedel–Crafts reaction">Friedel–Crafts reaction</a></li> <li><a href="/wiki/Fujimoto%E2%80%93Belleau_reaction" title="Fujimoto–Belleau reaction">Fujimoto–Belleau reaction</a></li> <li><a href="/wiki/Fujiwara%E2%80%93Moritani_reaction" title="Fujiwara–Moritani reaction">Fujiwara–Moritani reaction</a></li> <li><a href="/wiki/Fukuyama_coupling" title="Fukuyama coupling">Fukuyama coupling</a></li> <li><a href="/wiki/Gabriel%E2%80%93Colman_rearrangement" title="Gabriel–Colman rearrangement">Gabriel–Colman rearrangement</a></li> <li><a href="/wiki/Gattermann_reaction" title="Gattermann reaction">Gattermann reaction</a></li> <li><a href="/wiki/Glaser_coupling" title="Glaser coupling">Glaser coupling</a></li> <li><a href="/wiki/Grignard_reaction" title="Grignard reaction">Grignard reaction</a></li> <li><a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagent</a></li> <li><a href="/wiki/Hammick_reaction" title="Hammick reaction">Hammick reaction</a></li> <li><a href="/wiki/Heck_reaction" title="Heck reaction">Heck reaction</a></li> <li><a href="/wiki/Henry_reaction" title="Henry reaction">Henry reaction</a></li> <li><a href="/wiki/Heterogeneous_metal_catalyzed_cross-coupling" title="Heterogeneous metal catalyzed cross-coupling">Heterogeneous metal catalyzed cross-coupling</a></li> <li><a href="/wiki/High_dilution_principle" title="High dilution principle">High dilution principle</a></li> <li><a href="/wiki/Hiyama_coupling" title="Hiyama coupling">Hiyama coupling</a></li> <li><a href="/wiki/Homologation_reaction" title="Homologation reaction">Homologation reaction</a></li> <li><a href="/wiki/Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction" title="Horner–Wadsworth–Emmons reaction">Horner–Wadsworth–Emmons reaction</a></li> <li><a href="/wiki/Hydrocyanation" title="Hydrocyanation">Hydrocyanation</a></li> <li><a href="/wiki/Hydrovinylation" title="Hydrovinylation">Hydrovinylation</a></li> <li><a href="/wiki/Hydroxymethylation" title="Hydroxymethylation">Hydroxymethylation</a></li> <li><a href="/wiki/Ivanov_reaction" title="Ivanov reaction">Ivanov reaction</a></li> <li><a href="/wiki/Johnson%E2%80%93Corey%E2%80%93Chaykovsky_reaction" title="Johnson–Corey–Chaykovsky reaction">Johnson–Corey–Chaykovsky reaction</a></li> <li><a href="/wiki/Julia_olefination" title="Julia olefination">Julia olefination</a></li> <li><a href="/wiki/Julia%E2%80%93Kocienski_olefination" class="mw-redirect" title="Julia–Kocienski olefination">Julia–Kocienski olefination</a></li> <li><a href="/wiki/Kauffmann_olefination" title="Kauffmann olefination">Kauffmann olefination</a></li> <li><a href="/wiki/Knoevenagel_condensation" title="Knoevenagel condensation">Knoevenagel condensation</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Kolbe%E2%80%93Schmitt_reaction" title="Kolbe–Schmitt reaction">Kolbe–Schmitt reaction</a></li> <li><a href="/wiki/Kowalski_ester_homologation" title="Kowalski ester homologation">Kowalski ester homologation</a></li> <li><a href="/wiki/Kulinkovich_reaction" title="Kulinkovich reaction">Kulinkovich reaction</a></li> <li><a href="/wiki/Kumada_coupling" title="Kumada coupling">Kumada coupling</a></li> <li><a href="/wiki/Liebeskind%E2%80%93Srogl_coupling" title="Liebeskind–Srogl coupling">Liebeskind–Srogl coupling</a></li> <li><a href="/wiki/Malonic_ester_synthesis" title="Malonic ester synthesis">Malonic ester synthesis</a></li> <li><a href="/wiki/Mannich_reaction" title="Mannich reaction">Mannich reaction</a></li> <li><a href="/wiki/McMurry_reaction" title="McMurry reaction">McMurry reaction</a></li> <li><a href="/wiki/Meerwein_arylation" title="Meerwein arylation">Meerwein arylation</a></li> <li><a href="/wiki/Methylenation" title="Methylenation">Methylenation</a></li> <li><a href="/wiki/Michael_reaction" class="mw-redirect" title="Michael reaction">Michael reaction</a></li> <li><a href="/wiki/Minisci_reaction" title="Minisci reaction">Minisci reaction</a></li> <li><a href="/w/index.php?title=Mizoroki-Heck_vs._Reductive_Heck&action=edit&redlink=1" class="new" title="Mizoroki-Heck vs. Reductive Heck (page does not exist)">Mizoroki-Heck vs. Reductive Heck</a></li> <li><a href="/wiki/Nef_isocyanide_reaction" title="Nef isocyanide reaction">Nef isocyanide reaction</a></li> <li><a href="/wiki/Nef_synthesis" title="Nef synthesis">Nef synthesis</a></li> <li><a href="/wiki/Negishi_coupling" title="Negishi coupling">Negishi coupling</a></li> <li><a href="/wiki/Nierenstein_reaction" title="Nierenstein reaction">Nierenstein reaction</a></li> <li><a href="/wiki/Nitro-Mannich_reaction" title="Nitro-Mannich reaction">Nitro-Mannich reaction</a></li> <li><a href="/wiki/Nozaki%E2%80%93Hiyama%E2%80%93Kishi_reaction" title="Nozaki–Hiyama–Kishi reaction">Nozaki–Hiyama–Kishi reaction</a></li> <li><a href="/wiki/Olefin_conversion_technology" title="Olefin conversion technology">Olefin conversion technology</a></li> <li><a href="/wiki/Olefin_metathesis" title="Olefin metathesis">Olefin metathesis</a></li> <li><a href="/wiki/Palladium%E2%80%93NHC_complex" title="Palladium–NHC complex">Palladium–NHC complex</a></li> <li><a href="/wiki/Passerini_reaction" title="Passerini reaction">Passerini reaction</a></li> <li><a href="/wiki/Peterson_olefination" title="Peterson olefination">Peterson olefination</a></li> <li><a href="/wiki/Pfitzinger_reaction" title="Pfitzinger reaction">Pfitzinger reaction</a></li> <li><a href="/wiki/Piancatelli_rearrangement" title="Piancatelli rearrangement">Piancatelli rearrangement</a></li> <li><a href="/wiki/Pinacol_coupling_reaction" title="Pinacol coupling reaction">Pinacol coupling reaction</a></li> <li><a href="/wiki/Prins_reaction" title="Prins reaction">Prins reaction</a></li> <li><a href="/wiki/Quelet_reaction" title="Quelet reaction">Quelet reaction</a></li> <li><a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a></li> <li><a href="/wiki/Rauhut%E2%80%93Currier_reaction" title="Rauhut–Currier reaction">Rauhut–Currier reaction</a></li> <li><a href="/wiki/Reformatsky_reaction" title="Reformatsky reaction">Reformatsky reaction</a></li> <li><a href="/wiki/Reimer%E2%80%93Tiemann_reaction" title="Reimer–Tiemann reaction">Reimer–Tiemann reaction</a></li> <li><a href="/wiki/Rieche_formylation" title="Rieche formylation">Rieche formylation</a></li> <li><a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">Ring-closing metathesis</a></li> <li><a href="/wiki/Robinson_annulation" title="Robinson annulation">Robinson annulation</a></li> <li><a href="/wiki/Sakurai_reaction" title="Sakurai reaction">Sakurai reaction</a></li> <li><a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a></li> <li><a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a></li> <li><a href="/wiki/Sonogashira_coupling" title="Sonogashira coupling">Sonogashira coupling</a></li> <li><a href="/wiki/Stetter_reaction" title="Stetter reaction">Stetter reaction</a></li> <li><a href="/wiki/Stille_reaction" title="Stille reaction">Stille reaction</a></li> <li><a href="/wiki/Stoll%C3%A9_synthesis" title="Stollé synthesis">Stollé synthesis</a></li> <li><a href="/wiki/Stork_enamine_alkylation" title="Stork enamine alkylation">Stork enamine alkylation</a></li> <li><a href="/wiki/Suzuki_reaction" title="Suzuki reaction">Suzuki reaction</a></li> <li><a href="/wiki/Takai_olefination" title="Takai olefination">Takai olefination</a></li> <li><a href="/wiki/Thermal_rearrangement_of_aromatic_hydrocarbons" title="Thermal rearrangement of aromatic hydrocarbons">Thermal rearrangement of aromatic hydrocarbons</a></li> <li><a href="/wiki/Thorpe_reaction" title="Thorpe reaction">Thorpe reaction</a></li> <li><a href="/wiki/Ugi_reaction" title="Ugi reaction">Ugi reaction</a></li> <li><a href="/wiki/Ullmann_reaction" title="Ullmann reaction">Ullmann reaction</a></li> <li><a href="/wiki/Wagner-Jauregg_reaction" title="Wagner-Jauregg reaction">Wagner-Jauregg reaction</a></li> <li><a href="/wiki/Weinreb_ketone_synthesis" title="Weinreb ketone synthesis">Weinreb ketone synthesis</a></li> <li><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li> <li><a href="/wiki/Wurtz_reaction" title="Wurtz reaction">Wurtz reaction</a></li> <li><a href="/wiki/Wurtz%E2%80%93Fittig_reaction" title="Wurtz–Fittig reaction">Wurtz–Fittig reaction</a></li> <li><a href="/wiki/Zincke%E2%80%93Suhl_reaction" title="Zincke–Suhl reaction">Zincke–Suhl reaction</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Homologation_reactions" class="mw-redirect" title="Homologation reactions">Homologation reactions</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arndt%E2%80%93Eistert_reaction" title="Arndt–Eistert reaction">Arndt–Eistert reaction</a></li> <li><a href="/wiki/Hooker_reaction" title="Hooker reaction">Hooker reaction</a></li> <li><a href="/wiki/Kiliani%E2%80%93Fischer_synthesis" title="Kiliani–Fischer synthesis">Kiliani–Fischer synthesis</a></li> <li><a href="/wiki/Kowalski_ester_homologation" title="Kowalski ester homologation">Kowalski ester homologation</a></li> <li><a href="/wiki/Methoxymethylenetriphenylphosphorane" title="Methoxymethylenetriphenylphosphorane">Methoxymethylenetriphenylphosphorane</a></li> <li><a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a></li> <li><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Olefination reactions</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bamford%E2%80%93Stevens_reaction" title="Bamford–Stevens reaction">Bamford–Stevens reaction</a></li> <li><a href="/wiki/Barton%E2%80%93Kellogg_reaction" title="Barton–Kellogg reaction">Barton–Kellogg reaction</a></li> <li><a href="/wiki/Boord_olefin_synthesis" title="Boord olefin synthesis">Boord olefin synthesis</a></li> <li><a href="/wiki/Chugaev_elimination" title="Chugaev elimination">Chugaev elimination</a></li> <li><a href="/wiki/Cope_reaction" title="Cope reaction">Cope reaction</a></li> <li><a href="/wiki/Corey%E2%80%93Winter_olefin_synthesis" title="Corey–Winter olefin synthesis">Corey–Winter olefin synthesis</a></li> <li><a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">Dehydrohalogenation</a></li> <li><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reaction</a></li> <li><a href="/wiki/Grieco_elimination" title="Grieco elimination">Grieco elimination</a></li> <li><a href="/wiki/Hofmann_elimination" title="Hofmann elimination">Hofmann elimination</a></li> <li><a href="/wiki/Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction" title="Horner–Wadsworth–Emmons reaction">Horner–Wadsworth–Emmons reaction</a></li> <li><a href="/wiki/Hydrazone_iodination" title="Hydrazone iodination">Hydrazone iodination</a></li> <li><a href="/wiki/Julia_olefination" title="Julia olefination">Julia olefination</a></li> <li><a href="/wiki/Julia%E2%80%93Kocienski_olefination" class="mw-redirect" title="Julia–Kocienski olefination">Julia–Kocienski olefination</a></li> <li><a href="/wiki/Kauffmann_olefination" title="Kauffmann olefination">Kauffmann olefination</a></li> <li><a href="/wiki/McMurry_reaction" title="McMurry reaction">McMurry reaction</a></li> <li><a href="/wiki/Peterson_olefination" title="Peterson olefination">Peterson olefination</a></li> <li><a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a></li> <li><a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a></li> <li><a href="/wiki/Takai_olefination" title="Takai olefination">Takai olefination</a></li> <li><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em">Carbon-heteroatom <br /> bond forming <br /> reactions</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azo_coupling" title="Azo coupling">Azo coupling</a></li> <li><a href="/wiki/Bartoli_indole_synthesis" title="Bartoli indole synthesis">Bartoli indole synthesis</a></li> <li><a href="/wiki/Boudouard_reaction" title="Boudouard reaction">Boudouard reaction</a></li> <li><a href="/wiki/Cadogan%E2%80%93Sundberg_indole_synthesis" title="Cadogan–Sundberg indole synthesis">Cadogan–Sundberg indole synthesis</a></li> <li><a href="/wiki/Diazonium_compound" title="Diazonium compound">Diazonium compound</a></li> <li><a href="/wiki/Esterification" class="mw-redirect" title="Esterification">Esterification</a></li> <li><a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagent</a></li> <li><a href="/wiki/Haloform_reaction" title="Haloform reaction">Haloform reaction</a></li> <li><a href="/wiki/Hegedus_indole_synthesis" title="Hegedus indole synthesis">Hegedus indole synthesis</a></li> <li><a href="/wiki/Hurd%E2%80%93Mori_1,2,3-thiadiazole_synthesis" title="Hurd–Mori 1,2,3-thiadiazole synthesis">Hurd–Mori 1,2,3-thiadiazole synthesis</a></li> <li><a href="/wiki/Kharasch%E2%80%93Sosnovsky_reaction" title="Kharasch–Sosnovsky reaction">Kharasch–Sosnovsky reaction</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Leimgruber%E2%80%93Batcho_indole_synthesis" title="Leimgruber–Batcho indole synthesis">Leimgruber–Batcho indole synthesis</a></li> <li><a href="/wiki/Mukaiyama_hydration" title="Mukaiyama hydration">Mukaiyama hydration</a></li> <li><a href="/wiki/Nenitzescu_indole_synthesis" title="Nenitzescu indole synthesis">Nenitzescu indole synthesis</a></li> <li><a href="/wiki/Oxymercuration_reaction" title="Oxymercuration reaction">Oxymercuration reaction</a></li> <li><a href="/wiki/Reed_reaction" title="Reed reaction">Reed reaction</a></li> <li><a href="/wiki/Schotten%E2%80%93Baumann_reaction" title="Schotten–Baumann reaction">Schotten–Baumann reaction</a></li> <li><a href="/wiki/Ullmann_condensation" title="Ullmann condensation">Ullmann condensation</a></li> <li><a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a></li> <li><a href="/wiki/Yamaguchi_esterification" title="Yamaguchi esterification">Yamaguchi esterification</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em">Degradation <br /> reactions</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Barbier%E2%80%93Wieland_degradation" title="Barbier–Wieland degradation">Barbier–Wieland degradation</a></li> <li><a href="/wiki/Bergmann_degradation" title="Bergmann degradation">Bergmann degradation</a></li> <li><a href="/wiki/Edman_degradation" title="Edman degradation">Edman degradation</a></li> <li><a href="/wiki/Emde_degradation" title="Emde degradation">Emde degradation</a></li> <li><a href="/wiki/Gallagher%E2%80%93Hollander_degradation" title="Gallagher–Hollander degradation">Gallagher–Hollander degradation</a></li> <li><a href="/wiki/Hofmann_rearrangement" title="Hofmann rearrangement">Hofmann rearrangement</a></li> <li><a href="/wiki/Hooker_reaction" title="Hooker reaction">Hooker reaction</a></li> <li><a href="/wiki/Isosaccharinic_acid" title="Isosaccharinic acid">Isosaccharinic acid</a></li> <li><a href="/wiki/Marker_degradation" title="Marker degradation">Marker degradation</a></li> <li><a href="/wiki/Ruff_degradation" title="Ruff degradation">Ruff degradation</a></li> <li><a href="/wiki/Strecker_degradation" title="Strecker degradation">Strecker degradation</a></li> <li><a href="/wiki/Von_Braun_amide_degradation" title="Von Braun amide degradation">Von Braun amide degradation</a></li> <li><a href="/wiki/Weerman_degradation" title="Weerman degradation">Weerman degradation</a></li> <li><a href="/wiki/Wohl_degradation" title="Wohl degradation">Wohl degradation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em"><a href="/wiki/Organic_redox_reaction" title="Organic redox reaction">Organic redox <br /> reactions</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyloin_condensation" title="Acyloin condensation">Acyloin condensation</a></li> <li><a href="/wiki/Adkins%E2%80%93Peterson_reaction" title="Adkins–Peterson reaction">Adkins–Peterson reaction</a></li> <li><a href="/wiki/Akabori_amino-acid_reaction" title="Akabori amino-acid reaction">Akabori amino-acid reaction</a></li> <li><a href="/wiki/Alcohol_oxidation" title="Alcohol oxidation">Alcohol oxidation</a></li> <li><a href="/wiki/Algar%E2%80%93Flynn%E2%80%93Oyamada_reaction" title="Algar–Flynn–Oyamada reaction">Algar–Flynn–Oyamada reaction</a></li> <li><a href="/wiki/Amide_reduction" title="Amide reduction">Amide reduction</a></li> <li><a href="/wiki/Andrussow_process" title="Andrussow process">Andrussow process</a></li> <li><a href="/wiki/Angeli%E2%80%93Rimini_reaction" title="Angeli–Rimini reaction">Angeli–Rimini reaction</a></li> <li><a href="/wiki/Aromatization" title="Aromatization">Aromatization</a></li> <li><a href="/wiki/Autoxidation" title="Autoxidation">Autoxidation</a></li> <li><a href="/wiki/Baeyer%E2%80%93Villiger_oxidation" title="Baeyer–Villiger oxidation">Baeyer–Villiger oxidation</a></li> <li><a href="/wiki/Barton%E2%80%93McCombie_deoxygenation" title="Barton–McCombie deoxygenation">Barton–McCombie deoxygenation</a></li> <li><a href="/wiki/Bechamp_reduction" class="mw-redirect" title="Bechamp reduction">Bechamp reduction</a></li> <li><a href="/wiki/Benkeser_reaction" class="mw-redirect" title="Benkeser reaction">Benkeser reaction</a></li> <li><a href="/wiki/Bergmann_degradation" title="Bergmann degradation">Bergmann degradation</a></li> <li><a href="/wiki/Birch_reduction" title="Birch reduction">Birch reduction</a></li> <li><a href="/wiki/Bohn%E2%80%93Schmidt_reaction" title="Bohn–Schmidt reaction">Bohn–Schmidt reaction</a></li> <li><a href="/wiki/Bosch_reaction" title="Bosch reaction">Bosch reaction</a></li> <li><a href="/wiki/Bouveault%E2%80%93Blanc_reduction" title="Bouveault–Blanc reduction">Bouveault–Blanc reduction</a></li> <li><a href="/wiki/Boyland%E2%80%93Sims_oxidation" title="Boyland–Sims oxidation">Boyland–Sims oxidation</a></li> <li><a href="/wiki/Cannizzaro_reaction" title="Cannizzaro reaction">Cannizzaro reaction</a></li> <li><a href="/wiki/Carbonyl_reduction" title="Carbonyl reduction">Carbonyl reduction</a></li> <li><a href="/wiki/Clemmensen_reduction" title="Clemmensen reduction">Clemmensen reduction</a></li> <li><a href="/wiki/Collins_oxidation" title="Collins oxidation">Collins oxidation</a></li> <li><a href="/wiki/Corey%E2%80%93Itsuno_reduction" title="Corey–Itsuno reduction">Corey–Itsuno reduction</a></li> <li><a href="/wiki/Corey%E2%80%93Kim_oxidation" title="Corey–Kim oxidation">Corey–Kim oxidation</a></li> <li><a href="/wiki/Corey%E2%80%93Winter_olefin_synthesis" title="Corey–Winter olefin synthesis">Corey–Winter olefin synthesis</a></li> <li><a href="/wiki/Criegee_oxidation" title="Criegee oxidation">Criegee oxidation</a></li> <li><a href="/wiki/Dakin_oxidation" title="Dakin oxidation">Dakin oxidation</a></li> <li><a href="/wiki/Davis_oxidation" title="Davis oxidation">Davis oxidation</a></li> <li><a href="/wiki/Deoxygenation" title="Deoxygenation">Deoxygenation</a></li> <li><a href="/wiki/Dess%E2%80%93Martin_oxidation" title="Dess–Martin oxidation">Dess–Martin oxidation</a></li> <li><a href="/wiki/DNA_oxidation" title="DNA oxidation">DNA oxidation</a></li> <li><a href="/wiki/Elbs_persulfate_oxidation" title="Elbs persulfate oxidation">Elbs persulfate oxidation</a></li> <li><a href="/wiki/Emde_degradation" title="Emde degradation">Emde degradation</a></li> <li><a href="/wiki/Eschweiler%E2%80%93Clarke_reaction" title="Eschweiler–Clarke reaction">Eschweiler–Clarke reaction</a></li> <li><a href="/wiki/%C3%89tard_reaction" title="Étard reaction">Étard reaction</a></li> <li><a href="/wiki/Fischer%E2%80%93Tropsch_process" title="Fischer–Tropsch process">Fischer–Tropsch process</a></li> <li><a href="/wiki/Fleming%E2%80%93Tamao_oxidation" title="Fleming–Tamao oxidation">Fleming–Tamao oxidation</a></li> <li><a href="/wiki/Fukuyama_reduction" title="Fukuyama reduction">Fukuyama reduction</a></li> <li><a href="/wiki/Ganem_oxidation" title="Ganem oxidation">Ganem oxidation</a></li> <li><a href="/wiki/Glycol_cleavage" title="Glycol cleavage">Glycol cleavage</a></li> <li><a href="/wiki/Griesbaum_coozonolysis" title="Griesbaum coozonolysis">Griesbaum coozonolysis</a></li> <li><a href="/wiki/Grundmann_aldehyde_synthesis" title="Grundmann aldehyde synthesis">Grundmann aldehyde synthesis</a></li> <li><a href="/wiki/Haloform_reaction" title="Haloform reaction">Haloform reaction</a></li> <li><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a></li> <li><a href="/wiki/Hydrogenolysis" title="Hydrogenolysis">Hydrogenolysis</a></li> <li><a href="/wiki/Hydroxylation" title="Hydroxylation">Hydroxylation</a></li> <li><a href="/wiki/Jones_oxidation" title="Jones oxidation">Jones oxidation</a></li> <li><a href="/wiki/Kiliani%E2%80%93Fischer_synthesis" title="Kiliani–Fischer synthesis">Kiliani–Fischer synthesis</a></li> <li><a href="/wiki/Kolbe_electrolysis" title="Kolbe electrolysis">Kolbe electrolysis</a></li> <li><a href="/wiki/Kornblum_oxidation" title="Kornblum oxidation">Kornblum oxidation</a></li> <li><a href="/wiki/Kornblum%E2%80%93DeLaMare_rearrangement" title="Kornblum–DeLaMare rearrangement">Kornblum–DeLaMare rearrangement</a></li> <li><a href="/wiki/Leuckart_reaction" title="Leuckart reaction">Leuckart reaction</a></li> <li><a href="/wiki/Ley_oxidation" class="mw-redirect" title="Ley oxidation">Ley oxidation</a></li> <li><a href="/wiki/Lindgren_oxidation" title="Lindgren oxidation">Lindgren oxidation</a></li> <li><a href="/wiki/Lipid_peroxidation" title="Lipid peroxidation">Lipid peroxidation</a></li> <li><a href="/wiki/Lombardo_methylenation" title="Lombardo methylenation">Lombardo methylenation</a></li> <li><a href="/wiki/Luche_reduction" title="Luche reduction">Luche reduction</a></li> <li><a href="/wiki/Mark%C3%B3%E2%80%93Lam_deoxygenation" title="Markó–Lam deoxygenation">Markó–Lam deoxygenation</a></li> <li><a href="/wiki/McFadyen%E2%80%93Stevens_reaction" title="McFadyen–Stevens reaction">McFadyen–Stevens reaction</a></li> <li><a href="/wiki/Meerwein%E2%80%93Ponndorf%E2%80%93Verley_reduction" title="Meerwein–Ponndorf–Verley reduction">Meerwein–Ponndorf–Verley reduction</a></li> <li><a href="/wiki/Methionine_sulfoxide" title="Methionine sulfoxide">Methionine sulfoxide</a></li> <li><a href="/wiki/Miyaura_borylation" title="Miyaura borylation">Miyaura borylation</a></li> <li><a href="/wiki/Mozingo_reduction" title="Mozingo reduction">Mozingo reduction</a></li> <li><a href="/wiki/Noyori_asymmetric_hydrogenation" class="mw-redirect" title="Noyori asymmetric hydrogenation">Noyori asymmetric hydrogenation</a></li> <li><a href="/wiki/Omega_oxidation" title="Omega oxidation">Omega oxidation</a></li> <li><a href="/wiki/Oppenauer_oxidation" title="Oppenauer oxidation">Oppenauer oxidation</a></li> <li><a href="/wiki/Oxygen_rebound_mechanism" title="Oxygen rebound mechanism">Oxygen rebound mechanism</a></li> <li><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a></li> <li><a href="/wiki/Parikh%E2%80%93Doering_oxidation" title="Parikh–Doering oxidation">Parikh–Doering oxidation</a></li> <li><a href="/wiki/Pinnick_oxidation" title="Pinnick oxidation">Pinnick oxidation</a></li> <li><a href="/wiki/Pr%C3%A9vost_reaction" title="Prévost reaction">Prévost reaction</a></li> <li><a href="/wiki/Reduction_of_nitro_compounds" title="Reduction of nitro compounds">Reduction of nitro compounds</a></li> <li><a href="/wiki/Reductive_amination" title="Reductive amination">Reductive amination</a></li> <li><a href="/wiki/Riley_oxidation" title="Riley oxidation">Riley oxidation</a></li> <li><a href="/wiki/Rosenmund_reduction" title="Rosenmund reduction">Rosenmund reduction</a></li> <li><a href="/wiki/Rubottom_oxidation" title="Rubottom oxidation">Rubottom oxidation</a></li> <li><a href="/wiki/Sabatier_reaction" title="Sabatier reaction">Sabatier reaction</a></li> <li><a href="/wiki/Sarett_oxidation" title="Sarett oxidation">Sarett oxidation</a></li> <li><a href="/wiki/Selenoxide_elimination" title="Selenoxide elimination">Selenoxide elimination</a></li> <li><a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a></li> <li><a href="/wiki/Sharpless_asymmetric_dihydroxylation" title="Sharpless asymmetric dihydroxylation">Sharpless asymmetric dihydroxylation</a></li> <li><a href="/wiki/Epoxidation_of_allylic_alcohols" title="Epoxidation of allylic alcohols">Epoxidation of allylic alcohols</a></li> <li><a href="/wiki/Sharpless_epoxidation" title="Sharpless epoxidation">Sharpless epoxidation</a></li> <li><a href="/wiki/Sharpless_oxyamination" title="Sharpless oxyamination">Sharpless oxyamination</a></li> <li><a href="/wiki/Stahl_oxidation" title="Stahl oxidation">Stahl oxidation</a></li> <li><a href="/wiki/Staudinger_reaction" title="Staudinger reaction">Staudinger reaction</a></li> <li><a href="/wiki/Stephen_aldehyde_synthesis" title="Stephen aldehyde synthesis">Stephen aldehyde synthesis</a></li> <li><a href="/wiki/Swern_oxidation" title="Swern oxidation">Swern oxidation</a></li> <li><a href="/wiki/Transfer_hydrogenation" title="Transfer hydrogenation">Transfer hydrogenation</a></li> <li><a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a></li> <li><a href="/wiki/Wharton_reaction" title="Wharton reaction">Wharton reaction</a></li> <li><a href="/wiki/Whiting_reaction" title="Whiting reaction">Whiting reaction</a></li> <li><a href="/wiki/Wohl%E2%80%93Aue_reaction" title="Wohl–Aue reaction">Wohl–Aue reaction</a></li> <li><a href="/wiki/Wolff%E2%80%93Kishner_reduction" title="Wolff–Kishner reduction">Wolff–Kishner reduction</a></li> <li><a href="/wiki/Wolffenstein%E2%80%93B%C3%B6ters_reaction" title="Wolffenstein–Böters reaction">Wolffenstein–Böters reaction</a></li> <li><a href="/wiki/Zinin_reaction" title="Zinin reaction">Zinin reaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em"><a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">Rearrangement <br /> reactions</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,2-rearrangement" title="1,2-rearrangement">1,2-rearrangement</a></li> <li><a href="/wiki/1,2-Wittig_rearrangement" title="1,2-Wittig rearrangement">1,2-Wittig rearrangement</a></li> <li><a href="/wiki/2,3-sigmatropic_rearrangement" title="2,3-sigmatropic rearrangement">2,3-sigmatropic rearrangement</a></li> <li><a href="/wiki/2,3-Wittig_rearrangement" title="2,3-Wittig rearrangement">2,3-Wittig rearrangement</a></li> <li><a href="/wiki/Achmatowicz_reaction" title="Achmatowicz reaction">Achmatowicz reaction</a></li> <li><a href="/wiki/Alkyne_zipper_reaction" title="Alkyne zipper reaction">Alkyne zipper reaction</a></li> <li><a href="/wiki/Allen%E2%80%93Millar%E2%80%93Trippett_rearrangement" title="Allen–Millar–Trippett rearrangement">Allen–Millar–Trippett rearrangement</a></li> <li><a href="/wiki/Allylic_rearrangement" title="Allylic rearrangement">Allylic rearrangement</a></li> <li><a href="/wiki/Alpha-ketol_rearrangement" class="mw-redirect" title="Alpha-ketol rearrangement">Alpha-ketol rearrangement</a></li> <li><a href="/wiki/Amadori_rearrangement" title="Amadori rearrangement">Amadori rearrangement</a></li> <li><a href="/wiki/Arndt%E2%80%93Eistert_reaction" title="Arndt–Eistert reaction">Arndt–Eistert reaction</a></li> <li><a href="/wiki/Aza-Cope_rearrangement" title="Aza-Cope rearrangement">Aza-Cope rearrangement</a></li> <li><a href="/wiki/Baker%E2%80%93Venkataraman_rearrangement" title="Baker–Venkataraman rearrangement">Baker–Venkataraman rearrangement</a></li> <li><a href="/wiki/Bamberger_rearrangement" title="Bamberger rearrangement">Bamberger rearrangement</a></li> <li><a href="/wiki/Banert_cascade" title="Banert cascade">Banert cascade</a></li> <li><a href="/wiki/Beckmann_rearrangement" title="Beckmann rearrangement">Beckmann rearrangement</a></li> <li><a href="/wiki/Benzilic_acid_rearrangement" title="Benzilic acid rearrangement">Benzilic acid rearrangement</a></li> <li><a href="/wiki/Bergman_cyclization" title="Bergman cyclization">Bergman cyclization</a></li> <li><a href="/wiki/Bergmann_degradation" title="Bergmann degradation">Bergmann degradation</a></li> <li><a href="/wiki/Boekelheide_reaction" title="Boekelheide reaction">Boekelheide reaction</a></li> <li><a href="/wiki/Brook_rearrangement" title="Brook rearrangement">Brook rearrangement</a></li> <li><a href="/wiki/Buchner_ring_expansion" title="Buchner ring expansion">Buchner ring expansion</a></li> <li><a href="/wiki/Carroll_rearrangement" title="Carroll rearrangement">Carroll rearrangement</a></li> <li><a href="/wiki/Chan_rearrangement" title="Chan rearrangement">Chan rearrangement</a></li> <li><a href="/wiki/Claisen_rearrangement" title="Claisen rearrangement">Claisen rearrangement</a></li> <li><a href="/wiki/Cope_rearrangement" title="Cope rearrangement">Cope rearrangement</a></li> <li><a href="/wiki/Corey%E2%80%93Fuchs_reaction" title="Corey–Fuchs reaction">Corey–Fuchs reaction</a></li> <li><a href="/wiki/Cornforth_rearrangement" title="Cornforth rearrangement">Cornforth rearrangement</a></li> <li><a href="/wiki/Criegee_rearrangement" title="Criegee rearrangement">Criegee rearrangement</a></li> <li><a class="mw-selflink selflink">Curtius rearrangement</a></li> <li><a href="/wiki/Demjanov_rearrangement" title="Demjanov rearrangement">Demjanov rearrangement</a></li> <li><a href="/wiki/Di-%CF%80-methane_rearrangement" title="Di-π-methane rearrangement">Di-π-methane rearrangement</a></li> <li><a href="/wiki/Dimroth_rearrangement" title="Dimroth rearrangement">Dimroth rearrangement</a></li> <li><a href="/wiki/Divinylcyclopropane-cycloheptadiene_rearrangement" title="Divinylcyclopropane-cycloheptadiene rearrangement">Divinylcyclopropane-cycloheptadiene rearrangement</a></li> <li><a href="/wiki/Dowd%E2%80%93Beckwith_ring-expansion_reaction" title="Dowd–Beckwith ring-expansion reaction">Dowd–Beckwith ring-expansion reaction</a></li> <li><a href="/wiki/Electrocyclic_reaction" title="Electrocyclic reaction">Electrocyclic reaction</a></li> <li><a href="/wiki/Ene_reaction" title="Ene reaction">Ene reaction</a></li> <li><a href="/wiki/Enyne_metathesis" title="Enyne metathesis">Enyne metathesis</a></li> <li><a href="/wiki/Favorskii_reaction" title="Favorskii reaction">Favorskii reaction</a></li> <li><a href="/wiki/Favorskii_rearrangement" title="Favorskii rearrangement">Favorskii rearrangement</a></li> <li><a href="/wiki/Ferrier_carbocyclization" title="Ferrier carbocyclization">Ferrier carbocyclization</a></li> <li><a href="/wiki/Ferrier_rearrangement" title="Ferrier rearrangement">Ferrier rearrangement</a></li> <li><a href="/wiki/Fischer%E2%80%93Hepp_rearrangement" title="Fischer–Hepp rearrangement">Fischer–Hepp rearrangement</a></li> <li><a href="/wiki/Fries_rearrangement" title="Fries rearrangement">Fries rearrangement</a></li> <li><a href="/wiki/Fritsch%E2%80%93Buttenberg%E2%80%93Wiechell_rearrangement" title="Fritsch–Buttenberg–Wiechell rearrangement">Fritsch–Buttenberg–Wiechell rearrangement</a></li> <li><a href="/wiki/Gabriel%E2%80%93Colman_rearrangement" title="Gabriel–Colman rearrangement">Gabriel–Colman rearrangement</a></li> <li><a href="/wiki/Group_transfer_reaction" title="Group transfer reaction">Group transfer reaction</a></li> <li><a href="/wiki/Halogen_dance_rearrangement" title="Halogen dance rearrangement">Halogen dance rearrangement</a></li> <li><a href="/wiki/Hayashi_rearrangement" title="Hayashi rearrangement">Hayashi rearrangement</a></li> <li><a href="/wiki/Hofmann_rearrangement" title="Hofmann rearrangement">Hofmann rearrangement</a></li> <li><a href="/wiki/Hofmann%E2%80%93Martius_rearrangement" title="Hofmann–Martius rearrangement">Hofmann–Martius rearrangement</a></li> <li><a href="/wiki/Ireland%E2%80%93Claisen_rearrangement" title="Ireland–Claisen rearrangement">Ireland–Claisen rearrangement</a></li> <li><a href="/wiki/Jacobsen_rearrangement" title="Jacobsen rearrangement">Jacobsen rearrangement</a></li> <li><a href="/wiki/Kornblum%E2%80%93DeLaMare_rearrangement" title="Kornblum–DeLaMare rearrangement">Kornblum–DeLaMare rearrangement</a></li> <li><a href="/wiki/Kowalski_ester_homologation" title="Kowalski ester homologation">Kowalski ester homologation</a></li> <li><a href="/wiki/Lobry_de_Bruyn%E2%80%93Van_Ekenstein_transformation" title="Lobry de Bruyn–Van Ekenstein transformation">Lobry de Bruyn–Van Ekenstein transformation</a></li> <li><a href="/wiki/Lossen_rearrangement" title="Lossen rearrangement">Lossen rearrangement</a></li> <li><a href="/wiki/McFadyen%E2%80%93Stevens_reaction" title="McFadyen–Stevens reaction">McFadyen–Stevens reaction</a></li> <li><a href="/wiki/McLafferty_rearrangement" title="McLafferty rearrangement">McLafferty rearrangement</a></li> <li><a href="/wiki/Meyer%E2%80%93Schuster_rearrangement" title="Meyer–Schuster rearrangement">Meyer–Schuster rearrangement</a></li> <li><a href="/wiki/Mislow%E2%80%93Evans_rearrangement" title="Mislow–Evans rearrangement">Mislow–Evans rearrangement</a></li> <li><a href="/wiki/Mumm_rearrangement" title="Mumm rearrangement">Mumm rearrangement</a></li> <li><a href="/wiki/Myers_allene_synthesis" title="Myers allene synthesis">Myers allene synthesis</a></li> <li><a href="/wiki/Nazarov_cyclization_reaction" title="Nazarov cyclization reaction">Nazarov cyclization reaction</a></li> <li><a href="/wiki/Neber_rearrangement" title="Neber rearrangement">Neber rearrangement</a></li> <li><a href="/wiki/Newman%E2%80%93Kwart_rearrangement" title="Newman–Kwart rearrangement">Newman–Kwart rearrangement</a></li> <li><a href="/wiki/Overman_rearrangement" title="Overman rearrangement">Overman rearrangement</a></li> <li><a href="/wiki/Oxy-Cope_rearrangement" title="Oxy-Cope rearrangement">Oxy-Cope rearrangement</a></li> <li><a href="/wiki/Pericyclic_reaction" title="Pericyclic reaction">Pericyclic reaction</a></li> <li><a href="/wiki/Piancatelli_rearrangement" title="Piancatelli rearrangement">Piancatelli rearrangement</a></li> <li><a href="/wiki/Pinacol_rearrangement" title="Pinacol rearrangement">Pinacol rearrangement</a></li> <li><a href="/wiki/Pummerer_rearrangement" title="Pummerer rearrangement">Pummerer rearrangement</a></li> <li><a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a></li> <li><a href="/wiki/Ring_expansion_and_contraction" title="Ring expansion and contraction">Ring expansion and contraction</a></li> <li><a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">Ring-closing metathesis</a></li> <li><a href="/wiki/Rupe_reaction" class="mw-redirect" title="Rupe reaction">Rupe reaction</a></li> <li><a href="/wiki/Schmidt_reaction" title="Schmidt reaction">Schmidt reaction</a></li> <li><a href="/wiki/Semipinacol_rearrangement" title="Semipinacol rearrangement">Semipinacol rearrangement</a></li> <li><a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a></li> <li><a href="/wiki/Sigmatropic_reaction" title="Sigmatropic reaction">Sigmatropic reaction</a></li> <li><a href="/wiki/Skatteb%C3%B8l_rearrangement" title="Skattebøl rearrangement">Skattebøl rearrangement</a></li> <li><a href="/wiki/Smiles_rearrangement" title="Smiles rearrangement">Smiles rearrangement</a></li> <li><a href="/wiki/Sommelet%E2%80%93Hauser_rearrangement" title="Sommelet–Hauser rearrangement">Sommelet–Hauser rearrangement</a></li> <li><a href="/wiki/Stevens_rearrangement" title="Stevens rearrangement">Stevens rearrangement</a></li> <li><a href="/wiki/Stieglitz_rearrangement" title="Stieglitz rearrangement">Stieglitz rearrangement</a></li> <li><a href="/wiki/Thermal_rearrangement_of_aromatic_hydrocarbons" title="Thermal rearrangement of aromatic hydrocarbons">Thermal rearrangement of aromatic hydrocarbons</a></li> <li><a href="/wiki/Tiffeneau%E2%80%93Demjanov_rearrangement" title="Tiffeneau–Demjanov rearrangement">Tiffeneau–Demjanov rearrangement</a></li> <li><a href="/wiki/Vinylcyclopropane_rearrangement" title="Vinylcyclopropane rearrangement">Vinylcyclopropane rearrangement</a></li> <li><a href="/wiki/Wagner%E2%80%93Meerwein_rearrangement" title="Wagner–Meerwein rearrangement">Wagner–Meerwein rearrangement</a></li> <li><a href="/wiki/Wallach_rearrangement" title="Wallach rearrangement">Wallach rearrangement</a></li> <li><a href="/wiki/Weerman_degradation" title="Weerman degradation">Weerman degradation</a></li> <li><a href="/wiki/Westphalen%E2%80%93Lettr%C3%A9_rearrangement" title="Westphalen–Lettré rearrangement">Westphalen–Lettré rearrangement</a></li> <li><a href="/wiki/Willgerodt_rearrangement" title="Willgerodt rearrangement">Willgerodt rearrangement</a></li> <li><a href="/wiki/Wolff_rearrangement" title="Wolff rearrangement">Wolff rearrangement</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:7.5em"><a href="/wiki/Ring_forming_reaction" title="Ring forming reaction">Ring forming <br /> reactions</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,3-Dipolar_cycloaddition" title="1,3-Dipolar cycloaddition">1,3-Dipolar cycloaddition</a></li> <li><a href="/wiki/Annulation" title="Annulation">Annulation</a></li> <li><a href="/wiki/Azide-alkyne_Huisgen_cycloaddition" title="Azide-alkyne Huisgen cycloaddition">Azide-alkyne Huisgen cycloaddition</a></li> <li><a href="/wiki/Baeyer%E2%80%93Emmerling_indole_synthesis" title="Baeyer–Emmerling indole synthesis">Baeyer–Emmerling indole synthesis</a></li> <li><a href="/wiki/Bartoli_indole_synthesis" title="Bartoli indole synthesis">Bartoli indole synthesis</a></li> <li><a href="/wiki/Bergman_cyclization" title="Bergman cyclization">Bergman cyclization</a></li> <li><a href="/wiki/Biginelli_reaction" title="Biginelli reaction">Biginelli reaction</a></li> <li><a href="/wiki/Bischler%E2%80%93M%C3%B6hlau_indole_synthesis" title="Bischler–Möhlau indole synthesis">Bischler–Möhlau indole synthesis</a></li> <li><a href="/wiki/Bischler%E2%80%93Napieralski_reaction" title="Bischler–Napieralski reaction">Bischler–Napieralski reaction</a></li> <li><a href="/wiki/Blum%E2%80%93Ittah_aziridine_synthesis" title="Blum–Ittah aziridine synthesis">Blum–Ittah aziridine synthesis</a></li> <li><a href="/wiki/Bobbitt_reaction" title="Bobbitt reaction">Bobbitt reaction</a></li> <li><a href="/wiki/Bohlmann%E2%80%93Rahtz_pyridine_synthesis" title="Bohlmann–Rahtz pyridine synthesis">Bohlmann–Rahtz pyridine synthesis</a></li> <li><a href="/wiki/Borsche%E2%80%93Drechsel_cyclization" title="Borsche–Drechsel cyclization">Borsche–Drechsel cyclization</a></li> <li><a href="/wiki/Bucherer_carbazole_synthesis" title="Bucherer carbazole synthesis">Bucherer carbazole synthesis</a></li> <li><a href="/wiki/Bucherer%E2%80%93Bergs_reaction" title="Bucherer–Bergs reaction">Bucherer–Bergs reaction</a></li> <li><a href="/wiki/Cadogan%E2%80%93Sundberg_indole_synthesis" title="Cadogan–Sundberg indole synthesis">Cadogan–Sundberg indole synthesis</a></li> <li><a href="/wiki/Camps_quinoline_synthesis" title="Camps quinoline synthesis">Camps quinoline synthesis</a></li> <li><a href="/wiki/Chichibabin_pyridine_synthesis" title="Chichibabin pyridine synthesis">Chichibabin pyridine synthesis</a></li> <li><a href="/wiki/Cook%E2%80%93Heilbron_thiazole_synthesis" title="Cook–Heilbron thiazole synthesis">Cook–Heilbron thiazole synthesis</a></li> <li><a href="/wiki/Cycloaddition" title="Cycloaddition">Cycloaddition</a></li> <li><a href="/wiki/Darzens_reaction" title="Darzens reaction">Darzens reaction</a></li> <li><a href="/wiki/Davis%E2%80%93Beirut_reaction" title="Davis–Beirut reaction">Davis–Beirut reaction</a></li> <li><a href="/wiki/De_Kimpe_aziridine_synthesis" title="De Kimpe aziridine synthesis">De Kimpe aziridine synthesis</a></li> <li><a href="/wiki/Debus%E2%80%93Radziszewski_imidazole_synthesis" title="Debus–Radziszewski imidazole synthesis">Debus–Radziszewski imidazole synthesis</a></li> <li><a href="/wiki/Dieckmann_condensation" title="Dieckmann condensation">Dieckmann condensation</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Feist%E2%80%93Benary_synthesis" title="Feist–Benary synthesis">Feist–Benary synthesis</a></li> <li><a href="/wiki/Ferrario%E2%80%93Ackermann_reaction" title="Ferrario–Ackermann reaction">Ferrario–Ackermann reaction</a></li> <li><a href="/wiki/Fiesselmann_thiophene_synthesis" title="Fiesselmann thiophene synthesis">Fiesselmann thiophene synthesis</a></li> <li><a href="/wiki/Fischer_indole_synthesis" title="Fischer indole synthesis">Fischer indole synthesis</a></li> <li><a href="/wiki/Fischer_oxazole_synthesis" title="Fischer oxazole synthesis">Fischer oxazole synthesis</a></li> <li><a href="/wiki/Friedl%C3%A4nder_synthesis" title="Friedländer synthesis">Friedländer synthesis</a></li> <li><a href="/wiki/Gewald_reaction" title="Gewald reaction">Gewald reaction</a></li> <li><a href="/wiki/Graham_reaction" title="Graham reaction">Graham reaction</a></li> <li><a href="/wiki/Hantzsch_pyridine_synthesis" title="Hantzsch pyridine synthesis">Hantzsch pyridine synthesis</a></li> <li><a href="/wiki/Hegedus_indole_synthesis" title="Hegedus indole synthesis">Hegedus indole synthesis</a></li> <li><a href="/wiki/Hemetsberger_indole_synthesis" title="Hemetsberger indole synthesis">Hemetsberger indole synthesis</a></li> <li><a href="/wiki/Hofmann%E2%80%93L%C3%B6ffler_reaction" title="Hofmann–Löffler reaction">Hofmann–Löffler reaction</a></li> <li><a href="/wiki/Hurd%E2%80%93Mori_1,2,3-thiadiazole_synthesis" title="Hurd–Mori 1,2,3-thiadiazole synthesis">Hurd–Mori 1,2,3-thiadiazole synthesis</a></li> <li><a href="/wiki/Iodolactonization" title="Iodolactonization">Iodolactonization</a></li> <li><a href="/wiki/Isay_reaction" title="Isay reaction">Isay reaction</a></li> <li><a href="/wiki/Jacobsen_epoxidation" title="Jacobsen epoxidation">Jacobsen epoxidation</a></li> <li><a href="/wiki/Johnson%E2%80%93Corey%E2%80%93Chaykovsky_reaction" title="Johnson–Corey–Chaykovsky reaction">Johnson–Corey–Chaykovsky reaction</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Knorr_quinoline_synthesis" title="Knorr quinoline synthesis">Knorr quinoline synthesis</a></li> <li><a href="/wiki/Kr%C3%B6hnke_pyridine_synthesis" title="Kröhnke pyridine synthesis">Kröhnke pyridine synthesis</a></li> <li><a href="/wiki/Kulinkovich_reaction" title="Kulinkovich reaction">Kulinkovich reaction</a></li> <li><a href="/wiki/Larock_indole_synthesis" title="Larock indole synthesis">Larock indole synthesis</a></li> <li><a href="/wiki/Madelung_synthesis" title="Madelung synthesis">Madelung synthesis</a></li> <li><a href="/wiki/Nazarov_cyclization_reaction" title="Nazarov cyclization reaction">Nazarov cyclization reaction</a></li> <li><a href="/wiki/Nenitzescu_indole_synthesis" title="Nenitzescu indole synthesis">Nenitzescu indole synthesis</a></li> <li><a href="/wiki/Niementowski_quinazoline_synthesis" title="Niementowski quinazoline synthesis">Niementowski quinazoline synthesis</a></li> <li><a href="/wiki/Niementowski_quinoline_synthesis" title="Niementowski quinoline synthesis">Niementowski quinoline synthesis</a></li> <li><a href="/wiki/Paal%E2%80%93Knorr_synthesis" title="Paal–Knorr synthesis">Paal–Knorr synthesis</a></li> <li><a href="/wiki/Patern%C3%B2%E2%80%93B%C3%BCchi_reaction" title="Paternò–Büchi reaction">Paternò–Büchi reaction</a></li> <li><a href="/wiki/Pechmann_condensation" title="Pechmann condensation">Pechmann condensation</a></li> <li><a href="/wiki/Petrenko-Kritschenko_piperidone_synthesis" title="Petrenko-Kritschenko piperidone synthesis">Petrenko-Kritschenko piperidone synthesis</a></li> <li><a href="/wiki/Pictet%E2%80%93Spengler_reaction" title="Pictet–Spengler reaction">Pictet–Spengler reaction</a></li> <li><a href="/wiki/Pomeranz%E2%80%93Fritsch_reaction" title="Pomeranz–Fritsch reaction">Pomeranz–Fritsch reaction</a></li> <li><a href="/wiki/Prilezhaev_reaction" title="Prilezhaev reaction">Prilezhaev reaction</a></li> <li><a href="/wiki/Pschorr_cyclization" title="Pschorr cyclization">Pschorr cyclization</a></li> <li><a href="/wiki/Reissert_indole_synthesis" title="Reissert indole synthesis">Reissert indole synthesis</a></li> <li><a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">Ring-closing metathesis</a></li> <li><a href="/wiki/Robinson_annulation" title="Robinson annulation">Robinson annulation</a></li> <li><a href="/wiki/Sharpless_epoxidation" title="Sharpless epoxidation">Sharpless epoxidation</a></li> <li><a href="/wiki/Simmons%E2%80%93Smith_reaction" title="Simmons–Smith reaction">Simmons–Smith reaction</a></li> <li><a href="/wiki/Skraup_reaction" title="Skraup reaction">Skraup reaction</a></li> <li><a href="/wiki/Urech_hydantoin_synthesis" title="Urech hydantoin synthesis">Urech hydantoin synthesis</a></li> <li><a href="/wiki/Van_Leusen_reaction" title="Van Leusen reaction">Van Leusen reaction</a></li> <li><a href="/wiki/Wenker_synthesis" title="Wenker synthesis">Wenker synthesis</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cycloaddition" title="Cycloaddition">Cycloaddition</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,3-Dipolar_cycloaddition" title="1,3-Dipolar cycloaddition">1,3-Dipolar cycloaddition</a></li> <li><a href="/wiki/4%2B4_Photocycloaddition" title="4+4 Photocycloaddition">4+4 Photocycloaddition</a></li> <li><a href="/wiki/(4%2B3)_cycloaddition" title="(4+3) cycloaddition">(4+3) cycloaddition</a></li> <li><a href="/wiki/6%2B4_Cycloaddition" title="6+4 Cycloaddition">6+4 Cycloaddition</a></li> <li><a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Alkyne trimerisation</a></li> <li><a href="/wiki/Aza-Diels%E2%80%93Alder_reaction" title="Aza-Diels–Alder reaction">Aza-Diels–Alder reaction</a></li> <li><a href="/wiki/Azide-alkyne_Huisgen_cycloaddition" title="Azide-alkyne Huisgen cycloaddition">Azide-alkyne Huisgen cycloaddition</a></li> <li><a href="/wiki/Bradsher_cycloaddition" title="Bradsher cycloaddition">Bradsher cycloaddition</a></li> <li><a href="/wiki/Cheletropic_reaction" title="Cheletropic reaction">Cheletropic reaction</a></li> <li><a href="/wiki/Conia-ene_reaction" title="Conia-ene reaction">Conia-ene reaction</a></li> <li><a href="/wiki/Cyclopropanation" title="Cyclopropanation">Cyclopropanation</a></li> <li><a href="/wiki/Diazoalkane_1,3-dipolar_cycloaddition" title="Diazoalkane 1,3-dipolar cycloaddition">Diazoalkane 1,3-dipolar cycloaddition</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Enone%E2%80%93alkene_cycloadditions" title="Enone–alkene cycloadditions">Enone–alkene cycloadditions</a></li> <li><a href="/wiki/Hexadehydro_Diels%E2%80%93Alder_reaction" title="Hexadehydro Diels–Alder reaction">Hexadehydro Diels–Alder reaction</a></li> <li><a href="/wiki/Intramolecular_Diels%E2%80%93Alder_cycloaddition" title="Intramolecular Diels–Alder cycloaddition">Intramolecular Diels–Alder cycloaddition</a></li> <li><a href="/wiki/Inverse_electron-demand_Diels%E2%80%93Alder_reaction" title="Inverse electron-demand Diels–Alder reaction">Inverse electron-demand Diels–Alder reaction</a></li> <li><a href="/wiki/Ketene_cycloaddition" title="Ketene cycloaddition">Ketene cycloaddition</a></li> <li><a href="/wiki/McCormack_reaction" title="McCormack reaction">McCormack reaction</a></li> <li><a href="/wiki/Metal-centered_cycloaddition_reactions" title="Metal-centered cycloaddition reactions">Metal-centered cycloaddition reactions</a></li> <li><a href="/wiki/Nitrone-olefin_(3%2B2)_cycloaddition" title="Nitrone-olefin (3+2) cycloaddition">Nitrone-olefin (3+2) cycloaddition</a></li> <li><a href="/wiki/Oxo-Diels%E2%80%93Alder_reaction" title="Oxo-Diels–Alder reaction">Oxo-Diels–Alder reaction</a></li> <li><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a></li> <li><a href="/wiki/Pauson%E2%80%93Khand_reaction" title="Pauson–Khand reaction">Pauson–Khand reaction</a></li> <li><a href="/wiki/Povarov_reaction" title="Povarov reaction">Povarov reaction</a></li> <li><a href="/wiki/Prato_reaction" title="Prato reaction">Prato reaction</a></li> <li><a href="/wiki/Retro-Diels%E2%80%93Alder_reaction" title="Retro-Diels–Alder reaction">Retro-Diels–Alder reaction</a></li> <li><a href="/wiki/Staudinger_synthesis" title="Staudinger synthesis">Staudinger synthesis</a></li> <li><a href="/wiki/Trimethylenemethane_cycloaddition" title="Trimethylenemethane cycloaddition">Trimethylenemethane cycloaddition</a></li> <li><a href="/wiki/Vinylcyclopropane_(5%2B2)_cycloaddition" title="Vinylcyclopropane (5+2) cycloaddition">Vinylcyclopropane (5+2) cycloaddition</a></li> <li><a href="/wiki/Wagner-Jauregg_reaction" title="Wagner-Jauregg reaction">Wagner-Jauregg reaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Heterocycle forming reactions</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Algar%E2%80%93Flynn%E2%80%93Oyamada_reaction" title="Algar–Flynn–Oyamada reaction">Algar–Flynn–Oyamada reaction</a></li> <li><a href="/wiki/Allan%E2%80%93Robinson_reaction" title="Allan–Robinson reaction">Allan–Robinson reaction</a></li> <li><a href="/wiki/Auwers_synthesis" title="Auwers synthesis">Auwers synthesis</a></li> <li><a href="/wiki/Bamberger_triazine_synthesis" title="Bamberger triazine synthesis">Bamberger triazine synthesis</a></li> <li><a href="/wiki/Banert_cascade" title="Banert cascade">Banert cascade</a></li> <li><a href="/wiki/Barton%E2%80%93Zard_reaction" title="Barton–Zard reaction">Barton–Zard reaction</a></li> <li><a href="/wiki/Bernthsen_acridine_synthesis" title="Bernthsen acridine synthesis">Bernthsen acridine synthesis</a></li> <li><a href="/wiki/Bischler%E2%80%93Napieralski_reaction" title="Bischler–Napieralski reaction">Bischler–Napieralski reaction</a></li> <li><a href="/wiki/Bobbitt_reaction" title="Bobbitt reaction">Bobbitt reaction</a></li> <li><a href="/wiki/Boger_pyridine_synthesis" title="Boger pyridine synthesis">Boger pyridine synthesis</a></li> <li><a href="/wiki/Borsche%E2%80%93Drechsel_cyclization" title="Borsche–Drechsel cyclization">Borsche–Drechsel cyclization</a></li> <li><a href="/wiki/Bucherer_carbazole_synthesis" title="Bucherer carbazole synthesis">Bucherer carbazole synthesis</a></li> <li><a href="/wiki/Bucherer%E2%80%93Bergs_reaction" title="Bucherer–Bergs reaction">Bucherer–Bergs reaction</a></li> <li><a href="/wiki/Chichibabin_pyridine_synthesis" title="Chichibabin pyridine synthesis">Chichibabin pyridine synthesis</a></li> <li><a href="/wiki/Cook%E2%80%93Heilbron_thiazole_synthesis" title="Cook–Heilbron thiazole synthesis">Cook–Heilbron thiazole synthesis</a></li> <li><a href="/wiki/Diazoalkane_1,3-dipolar_cycloaddition" title="Diazoalkane 1,3-dipolar cycloaddition">Diazoalkane 1,3-dipolar cycloaddition</a></li> <li><a href="/wiki/Einhorn%E2%80%93Brunner_reaction" title="Einhorn–Brunner reaction">Einhorn–Brunner reaction</a></li> <li><a href="/wiki/Erlenmeyer%E2%80%93Pl%C3%B6chl_azlactone_and_amino-acid_synthesis" title="Erlenmeyer–Plöchl azlactone and amino-acid synthesis">Erlenmeyer–Plöchl azlactone and amino-acid synthesis</a></li> <li><a href="/wiki/Feist%E2%80%93Benary_synthesis" title="Feist–Benary synthesis">Feist–Benary synthesis</a></li> <li><a href="/wiki/Fischer_oxazole_synthesis" title="Fischer oxazole synthesis">Fischer oxazole synthesis</a></li> <li><a href="/wiki/Gabriel%E2%80%93Colman_rearrangement" title="Gabriel–Colman rearrangement">Gabriel–Colman rearrangement</a></li> <li><a href="/wiki/Gewald_reaction" title="Gewald reaction">Gewald reaction</a></li> <li><a href="/wiki/Hantzsch_ester" title="Hantzsch ester">Hantzsch ester</a></li> <li><a href="/wiki/Hantzsch_pyridine_synthesis" title="Hantzsch pyridine synthesis">Hantzsch pyridine synthesis</a></li> <li><a href="/wiki/Herz_reaction" title="Herz reaction">Herz reaction</a></li> <li><a href="/wiki/Knorr_pyrrole_synthesis" title="Knorr pyrrole synthesis">Knorr pyrrole synthesis</a></li> <li><a href="/wiki/Kr%C3%B6hnke_pyridine_synthesis" title="Kröhnke pyridine synthesis">Kröhnke pyridine synthesis</a></li> <li><a href="/wiki/Lectka_enantioselective_beta-lactam_synthesis" title="Lectka enantioselective beta-lactam synthesis">Lectka enantioselective beta-lactam synthesis</a></li> <li><a href="/wiki/Lehmstedt%E2%80%93Tanasescu_reaction" title="Lehmstedt–Tanasescu reaction">Lehmstedt–Tanasescu reaction</a></li> <li><a href="/wiki/Niementowski_quinazoline_synthesis" title="Niementowski quinazoline synthesis">Niementowski quinazoline synthesis</a></li> <li><a href="/wiki/Nitrone-olefin_(3%2B2)_cycloaddition" title="Nitrone-olefin (3+2) cycloaddition">Nitrone-olefin (3+2) cycloaddition</a></li> <li><a href="/wiki/Paal%E2%80%93Knorr_synthesis" title="Paal–Knorr synthesis">Paal–Knorr synthesis</a></li> <li><a href="/wiki/Pellizzari_reaction" title="Pellizzari reaction">Pellizzari reaction</a></li> <li><a href="/wiki/Pictet%E2%80%93Spengler_reaction" title="Pictet–Spengler reaction">Pictet–Spengler reaction</a></li> <li><a href="/wiki/Pomeranz%E2%80%93Fritsch_reaction" title="Pomeranz–Fritsch reaction">Pomeranz–Fritsch reaction</a></li> <li><a href="/wiki/Prilezhaev_reaction" title="Prilezhaev reaction">Prilezhaev reaction</a></li> <li><a href="/wiki/Robinson%E2%80%93Gabriel_synthesis" title="Robinson–Gabriel synthesis">Robinson–Gabriel synthesis</a></li> <li><a href="/wiki/Stoll%C3%A9_synthesis" title="Stollé synthesis">Stollé synthesis</a></li> <li><a href="/wiki/Urech_hydantoin_synthesis" title="Urech hydantoin synthesis">Urech hydantoin synthesis</a></li> <li><a href="/wiki/Wenker_synthesis" title="Wenker synthesis">Wenker synthesis</a></li> <li><a href="/wiki/Wohl%E2%80%93Aue_reaction" title="Wohl–Aue reaction">Wohl–Aue reaction</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr></tbody></table><div> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q254370#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" 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