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Schmidt reaction - Wikipedia
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class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Schmidt reaction</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. 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href="https://de.wikipedia.org/wiki/Schmidt-Reaktion" title="Schmidt-Reaktion – German" lang="de" hreflang="de" data-title="Schmidt-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/Reacci%C3%B3n_de_Schmidt" title="Reacción de Schmidt – Spanish" lang="es" hreflang="es" data-title="Reacción de Schmidt" 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/%D9%88%D8%A7%DA%A9%D9%86%D8%B4_%D8%A7%D8%B4%D9%85%DB%8C%D8%AA" title="واکنش اشمیت – Persian" lang="fa" hreflang="fa" data-title="واکنش اشمیت" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B7%E3%83%A5%E3%83%9F%E3%83%83%E3%83%88%E5%8F%8D%E5%BF%9C" title="シュミット反応 – Japanese" lang="ja" hreflang="ja" data-title="シュミット反応" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Rea%C3%A7%C3%A3o_de_Schmidt" title="Reação de Schmidt – Portuguese" lang="pt" hreflang="pt" data-title="Reação de Schmidt" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Reac%C8%9Bie_Schmidt" title="Reacție Schmidt – Romanian" lang="ro" hreflang="ro" data-title="Reacție Schmidt" 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/Schmidt-reaktio" title="Schmidt-reaktio – Finnish" lang="fi" hreflang="fi" data-title="Schmidt-reaktio" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%96%BD%E5%AF%86%E7%89%B9%E5%8F%8D%E5%BA%94" title="施密特反应 – Chinese" lang="zh" hreflang="zh" data-title="施密特反应" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q903020#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> 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searchaux" style="display:none">Chemical reaction between an azide and a carbonyl derivative</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">Schmidt reaction </th></tr> <tr> <td>Named after </td> <td>Karl Friedrich Schmidt </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/schmidt-reaction.shtm">schmidt-reaction</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_0000170">RXNO:0000170</a></span> </td></tr> <tr> <td style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2"> </td></tr> </tbody></table> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, the <b>Schmidt reaction</b> is an <a href="/wiki/Organic_reaction" title="Organic reaction">organic reaction</a> in which an <a href="/wiki/Azide" title="Azide">azide</a> reacts with a <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> derivative, usually an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a>, <a href="/wiki/Ketone" title="Ketone">ketone</a>, or <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>, under acidic conditions to give an <a href="/wiki/Amine" title="Amine">amine</a> or <a href="/wiki/Amide" title="Amide">amide</a>, with expulsion of <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>.<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-Wolff2011_2-0" class="reference"><a href="#cite_note-Wolff2011-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is named after <a href="/w/index.php?title=Karl_Friedrich_Schmidt&action=edit&redlink=1" class="new" title="Karl Friedrich Schmidt (page does not exist)">Karl Friedrich Schmidt</a> (1887–1971), who first reported it in 1924 by successfully converting <a href="/wiki/Benzophenone" title="Benzophenone">benzophenone</a> and <a href="/wiki/Hydrazoic_acid" title="Hydrazoic acid">hydrazoic acid</a> to <a href="/wiki/Benzanilide" title="Benzanilide">benzanilide</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">intramolecular reaction</a> was not reported until 1991<sup id="cite_ref-intra_5-0" class="reference"><a href="#cite_note-intra-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> but has become important in the synthesis of natural products.<sup id="cite_ref-intra-review_6-0" class="reference"><a href="#cite_note-intra-review-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The reaction is effective with <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> to give amines (above), and with <a href="/wiki/Ketone" title="Ketone">ketones</a> to give amides (below). </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Schmidt_Reaktion_%C3%9Cbersicht_Carbons%C3%A4uren1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Schmidt_Reaktion_%C3%9Cbersicht_Carbons%C3%A4uren1.svg/350px-Schmidt_Reaktion_%C3%9Cbersicht_Carbons%C3%A4uren1.svg.png" decoding="async" width="350" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Schmidt_Reaktion_%C3%9Cbersicht_Carbons%C3%A4uren1.svg/525px-Schmidt_Reaktion_%C3%9Cbersicht_Carbons%C3%A4uren1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Schmidt_Reaktion_%C3%9Cbersicht_Carbons%C3%A4uren1.svg/700px-Schmidt_Reaktion_%C3%9Cbersicht_Carbons%C3%A4uren1.svg.png 2x" data-file-width="333" data-file-height="114" /></a><figcaption></figcaption></figure> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Schmidt_Reaktion_%C3%9Cbersicht_Ketone1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Schmidt_Reaktion_%C3%9Cbersicht_Ketone1.svg/400px-Schmidt_Reaktion_%C3%9Cbersicht_Ketone1.svg.png" decoding="async" width="400" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Schmidt_Reaktion_%C3%9Cbersicht_Ketone1.svg/600px-Schmidt_Reaktion_%C3%9Cbersicht_Ketone1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/Schmidt_Reaktion_%C3%9Cbersicht_Ketone1.svg/800px-Schmidt_Reaktion_%C3%9Cbersicht_Ketone1.svg.png 2x" data-file-width="370" data-file-height="125" /></a><figcaption></figcaption></figure> <meta property="mw:PageProp/toc" /> <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=Schmidt_reaction&action=edit&section=1" title="Edit section: Reaction mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The reaction is closely related to the <a href="/wiki/Curtius_rearrangement" title="Curtius rearrangement">Curtius rearrangement</a> except that in this reaction the acyl azide is produced by reaction of the carboxylic acid with hydrazoic acid via the protonated carboxylic acid, in a process akin to a <a href="/wiki/Fischer%E2%80%93Speier_esterification" title="Fischer–Speier esterification">Fischer esterification</a>. An alternative, involving the formation of an acylium ion, becomes more important when the reaction takes place in concentrated acid (>90% <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</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> (In the Curtius rearrangement, sodium azide and an acyl chloride are combined to quantitatively generate the acyl azide intermediate, and the rest of the reaction takes place under neutral conditions.) </p><p>The carboxylic acid Schmidt reaction starts with <a href="/wiki/Acylium" class="mw-redirect" title="Acylium">acylium</a> ion <b>1</b> obtained from <a href="/wiki/Protonation" title="Protonation">protonation</a> and loss of water. Reaction with <a href="/wiki/Hydrazoic_acid" title="Hydrazoic acid">hydrazoic acid</a> forms the protonated azido ketone <b>2</b>, which goes through a <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearrangement reaction</a> with the alkyl group R, migrating over the C-N bond with expulsion of nitrogen. The protonated <a href="/wiki/Isocyanate" title="Isocyanate">isocyanate</a> is attacked by water forming <a href="/wiki/Carbamate" title="Carbamate">carbamate</a> <b>4</b>, which after deprotonation loses <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> to the <a href="/wiki/Amine" title="Amine">amine</a>. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Schmidt_reaction_mechanism.svg" class="mw-file-description" title="Reaction mechanism for the amine formation from a carboxylic acid via Schmidt reaction."><img alt="Reaction mechanism for the amine formation from a carboxylic acid via Schmidt reaction." src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Schmidt_reaction_mechanism.svg/500px-Schmidt_reaction_mechanism.svg.png" decoding="async" width="500" height="295" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Schmidt_reaction_mechanism.svg/750px-Schmidt_reaction_mechanism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Schmidt_reaction_mechanism.svg/1000px-Schmidt_reaction_mechanism.svg.png 2x" data-file-width="451" data-file-height="266" /></a><figcaption>Reaction mechanism for the amine formation from a carboxylic acid via Schmidt reaction.</figcaption></figure> <p>In the reaction mechanism for the Schmidt reaction of <a href="/wiki/Ketone" title="Ketone">ketones</a>, the carbonyl group is activated by protonation for <a href="/wiki/Nucleophilic_addition" title="Nucleophilic addition">nucleophilic addition</a> by the azide, forming azidohydrin <b>3</b>, which loses water in an <a href="/wiki/Elimination_reaction" title="Elimination reaction">elimination reaction</a> to diazoiminium 5. One of the alkyl or aryl groups migrates from carbon to nitrogen with loss of nitrogen to give a nitrilium intermediate <b>6</b>, as in the <a href="/wiki/Beckmann_rearrangement" title="Beckmann rearrangement">Beckmann rearrangement</a>. Attack by water converts <b>6</b> to protonated imidic acid <b>7</b>, which undergoes loss of proton to arrive at the imidic acid <a href="/wiki/Tautomer" title="Tautomer">tautomer</a> of the final <a href="/wiki/Amide" title="Amide">amide</a>. In an alternative mechanism, the migration occurs at <b>9</b>, directly after protonation of intermediate <b>3</b>, in a manner similar to the <a href="/wiki/Baeyer%E2%80%93Villiger_oxidation" title="Baeyer–Villiger oxidation">Baeyer–Villiger oxidation</a> to give protonated amide <b>10</b>. Loss of a proton again furnishes the amide. It has been proposed that the dehydration to <b>3</b> to give <b>5</b> (and, hence, the Beckmann pathway) is favored by nonaqueous acids like conc. H<sub>2</sub>SO<sub>4</sub>, while aqueous acids like conc. HCl favor migration from <b>9</b> (the Baeyer-Villiger pathway). These possibilities have been used to account for the fact that, for certain substrates like <a href="/wiki/1-tetralone" class="mw-redirect" title="1-tetralone">α-tetralone</a>, the group that migrates can sometimes change, depending on the conditions used, to deliver either of the two possible amides.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Schmidt_reaction_mechanism_2.svg" class="mw-file-description" title="Two proposed reaction mechanisms for the amide formation from a ketone via Schmidt reaction"><img alt="Two proposed reaction mechanisms for the amide formation from a ketone via Schmidt reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Schmidt_reaction_mechanism_2.svg/650px-Schmidt_reaction_mechanism_2.svg.png" decoding="async" width="650" height="335" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Schmidt_reaction_mechanism_2.svg/975px-Schmidt_reaction_mechanism_2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/15/Schmidt_reaction_mechanism_2.svg/1300px-Schmidt_reaction_mechanism_2.svg.png 2x" data-file-width="586" data-file-height="302" /></a><figcaption>Two proposed reaction mechanisms for the amide formation from a ketone via Schmidt reaction</figcaption></figure> <p><br /> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions_involving_alkyl_azides">Reactions involving alkyl azides</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Schmidt_reaction&action=edit&section=2" title="Edit section: Reactions involving alkyl azides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The scope of this reaction has been extended to reactions of carbonyls with alkyl <a href="/wiki/Azides" class="mw-redirect" title="Azides">azides</a> R-N<sub>3</sub>. This extension was first reported by J.H. Boyer in 1955 <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> (hence the name <b>Boyer reaction</b>), for example, the reaction of <a href="/wiki/3-nitrobenzaldehyde" class="mw-redirect" title="3-nitrobenzaldehyde">3-nitrobenzaldehyde</a> with β-azido ethanol: </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:BoyerReaction.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/BoyerReaction.png/400px-BoyerReaction.png" decoding="async" width="400" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/BoyerReaction.png/600px-BoyerReaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/c/c6/BoyerReaction.png 2x" data-file-width="800" data-file-height="212" /></a><figcaption>The Boyer reaction</figcaption></figure> <p>Variations involving intramolecular Schmidt reactions have been known since 1991.<sup id="cite_ref-intra_5-1" class="reference"><a href="#cite_note-intra-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> These are <a href="/wiki/Annulation" title="Annulation">annulation</a> reactions and have some utility in the synthesis of natural products;<sup id="cite_ref-intra-review_6-1" class="reference"><a href="#cite_note-intra-review-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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> such as <a href="/wiki/Lactam" title="Lactam">lactams</a><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> and <a href="/wiki/Alkaloids" class="mw-redirect" title="Alkaloids">alkaloids</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:SchmidtreactionApplication.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/SchmidtreactionApplication.png/400px-SchmidtreactionApplication.png" decoding="async" width="400" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/SchmidtreactionApplication.png/600px-SchmidtreactionApplication.png 1.5x, //upload.wikimedia.org/wikipedia/commons/7/7a/SchmidtreactionApplication.png 2x" data-file-width="800" data-file-height="290" /></a><figcaption>Intramolecular Schmidt reaction</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=Schmidt_reaction&action=edit&section=3" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Curtius_rearrangement" title="Curtius rearrangement">Curtius rearrangement</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></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=Schmidt_reaction&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px 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="CITEREFPlagens,_AndreasLaue,_Thomas_M.2005" class="citation book cs1">Plagens, Andreas; Laue, Thomas M. (2005). <i>Named organic reactions</i> (2nd ed.). Chichester: John Wiley & Sons. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-470-01041-X" title="Special:BookSources/0-470-01041-X"><bdi>0-470-01041-X</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Named+organic+reactions&rft.place=Chichester&rft.edition=2nd&rft.pub=John+Wiley+%26+Sons&rft.date=2005&rft.isbn=0-470-01041-X&rft.au=Plagens%2C+Andreas&rft.au=Laue%2C+Thomas+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchmidt+reaction" class="Z3988"></span></span> </li> <li id="cite_note-Wolff2011-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Wolff2011_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWolff2011" class="citation journal cs1">Wolff, Hans (2011). "The Schmidt Reaction". <i>Organic Reactions</i>: 307–336. <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%2F0471264180.or003.08">10.1002/0471264180.or003.08</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0471264187" title="Special:BookSources/978-0471264187"><bdi>978-0471264187</bdi></a>.</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+Schmidt+Reaction&rft.pages=307-336&rft.date=2011&rft_id=info%3Adoi%2F10.1002%2F0471264180.or003.08&rft.isbn=978-0471264187&rft.aulast=Wolff&rft.aufirst=Hans&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchmidt+reaction" 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="CITEREFLangMurphy2006" class="citation journal cs1">Lang, S.; Murphy, J. A. (2006). "Azide rearrangements in electron-deficient systems". <i>Chem. Soc. Rev</i>. <b>35</b> (2): 146–156. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FB505080D">10.1039/B505080D</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/16444296">16444296</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Soc.+Rev.&rft.atitle=Azide+rearrangements+in+electron-deficient+systems&rft.volume=35&rft.issue=2&rft.pages=146-156&rft.date=2006&rft_id=info%3Adoi%2F10.1039%2FB505080D&rft_id=info%3Apmid%2F16444296&rft.aulast=Lang&rft.aufirst=S.&rft.au=Murphy%2C+J.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchmidt+reaction" 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="CITEREFSchmidt1924" class="citation journal cs1">Schmidt, K. F. (1924). "Über den Imin-Rest". <i>Berichte der Deutschen Chemischen Gesellschaft (A and B Series)</i>. <b>57</b> (4): 704–723. <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.19240570423">10.1002/cber.19240570423</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+%28A+and+B+Series%29&rft.atitle=%C3%9Cber+den+Imin-Rest&rft.volume=57&rft.issue=4&rft.pages=704-723&rft.date=1924&rft_id=info%3Adoi%2F10.1002%2Fcber.19240570423&rft.aulast=Schmidt&rft.aufirst=K.+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchmidt+reaction" class="Z3988"></span></span> </li> <li id="cite_note-intra-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-intra_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-intra_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJeffrey_AubeGregory_L._Milligan1991" class="citation journal cs1">Jeffrey Aube & Gregory L. Milligan (1991). "Intramolecular Schmidt reaction of alkyl azides". <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a></i> <b>113</b> (23): 8965–8966. <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%2Fja00023a065">10.1021/ja00023a065</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=Intramolecular+Schmidt+reaction+of+alkyl+azides&rft.volume=113&rft.issue=23&rft.pages=8965-8966&rft.date=1991&rft_id=info%3Adoi%2F10.1021%2Fja00023a065&rft.au=Jeffrey+Aube&rft.au=Gregory+L.+Milligan&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchmidt+reaction" class="Z3988"></span></span> </li> <li id="cite_note-intra-review-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-intra-review_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-intra-review_6-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNyfelerRenaud2006" class="citation journal cs1">Nyfeler, Erich; Renaud, Philippe (24 May 2006). <a rel="nofollow" class="external text" href="https://doi.org/10.2533%2F000942906777674714">"Intramolecular Schmidt Reaction: Applications in Natural Product Synthesis"</a>. <i>CHIMIA International Journal for Chemistry</i>. <b>60</b> (5): 276–284. <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/10.2533%2F000942906777674714">10.2533/000942906777674714</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=CHIMIA+International+Journal+for+Chemistry&rft.atitle=Intramolecular+Schmidt+Reaction%3A+Applications+in+Natural+Product+Synthesis&rft.volume=60&rft.issue=5&rft.pages=276-284&rft.date=2006-05-24&rft_id=info%3Adoi%2F10.2533%2F000942906777674714&rft.aulast=Nyfeler&rft.aufirst=Erich&rft.au=Renaud%2C+Philippe&rft_id=https%3A%2F%2Fdoi.org%2F10.2533%252F000942906777674714&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchmidt+reaction" 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="CITEREFKoldobskiiOstrovskiiGidaspov1978" class="citation journal cs1">Koldobskii, G I; Ostrovskii, Vladimir A; Gidaspov, B V (1978-11-30). "Schmidt Reaction with Aldehydes and Carboxylic Acids". <i>Russian Chemical Reviews</i>. <b>47</b> (11): 1084–1094. <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/1978RuCRv..47.1084K">1978RuCRv..47.1084K</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1070%2Frc1978v047n11abeh002294">10.1070/rc1978v047n11abeh002294</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0036-021X">0036-021X</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:250898289">250898289</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Russian+Chemical+Reviews&rft.atitle=Schmidt+Reaction+with+Aldehydes+and+Carboxylic+Acids&rft.volume=47&rft.issue=11&rft.pages=1084-1094&rft.date=1978-11-30&rft_id=info%3Adoi%2F10.1070%2Frc1978v047n11abeh002294&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A250898289%23id-name%3DS2CID&rft.issn=0036-021X&rft_id=info%3Abibcode%2F1978RuCRv..47.1084K&rft.aulast=Koldobskii&rft.aufirst=G+I&rft.au=Ostrovskii%2C+Vladimir+A&rft.au=Gidaspov%2C+B+V&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchmidt+reaction" 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="CITEREFCrosbyShinCapuano2010" class="citation journal cs1">Crosby, Ian T.; Shin, James K.; Capuano, Ben (2010). "The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations". <i>Australian Journal of Chemistry</i>. <b>63</b> (2): 211. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1071%2FCH09402">10.1071/CH09402</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0004-9425">0004-9425</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Australian+Journal+of+Chemistry&rft.atitle=The+Application+of+the+Schmidt+Reaction+and+Beckmann+Rearrangement+to+the+Synthesis+of+Bicyclic+Lactams%3A+Some+Mechanistic+Considerations&rft.volume=63&rft.issue=2&rft.pages=211&rft.date=2010&rft_id=info%3Adoi%2F10.1071%2FCH09402&rft.issn=0004-9425&rft.aulast=Crosby&rft.aufirst=Ian+T.&rft.au=Shin%2C+James+K.&rft.au=Capuano%2C+Ben&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchmidt+reaction" 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="CITEREFJ._H._BoyerJ._Hamer1955" class="citation journal cs1">J. H. Boyer & J. Hamer (1955). "The Acid-catalyzed Reaction of Alkyl Azides upon Carbonyl Compounds". <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a></i> <b>77</b> (4): 951–954. <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%2Fja01609a045">10.1021/ja01609a045</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+Acid-catalyzed+Reaction+of+Alkyl+Azides+upon+Carbonyl+Compounds&rft.volume=77&rft.issue=4&rft.pages=951-954&rft.date=1955&rft_id=info%3Adoi%2F10.1021%2Fja01609a045&rft.au=J.+H.+Boyer&rft.au=J.+Hamer&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchmidt+reaction" 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="CITEREFMilliganMossmanAube1995" class="citation journal cs1">Milligan, Gregory L.; Mossman, Craig J.; Aube, Jeffrey (October 1995). "Intramolecular Schmidt Reactions of Alkyl Azides with Ketones: Scope and Stereochemical Studies". <i>Journal of the American Chemical Society</i>. <b>117</b> (42): 10449–10459. <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%2Fja00147a006">10.1021/ja00147a006</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Intramolecular+Schmidt+Reactions+of+Alkyl+Azides+with+Ketones%3A+Scope+and+Stereochemical+Studies&rft.volume=117&rft.issue=42&rft.pages=10449-10459&rft.date=1995-10&rft_id=info%3Adoi%2F10.1021%2Fja00147a006&rft.aulast=Milligan&rft.aufirst=Gregory+L.&rft.au=Mossman%2C+Craig+J.&rft.au=Aube%2C+Jeffrey&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchmidt+reaction" 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="CITEREFLei_YaoJeffrey_Aubé2007" class="citation journal cs1">Lei Yao & Jeffrey Aubé (2007). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2596723">"Cation–π Control of Regiochemistry of Intramolecular Schmidt Reactions en Route to Bridged Bicyclic Lactams"</a> <span class="cs1-format">(Communication)</span>. <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a></i> <b>129</b> (10): 2766–2767. <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%2Fja068919r">10.1021/ja068919r</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2596723">2596723</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17302421">17302421</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=Cation%E2%80%93%CF%80+Control+of+Regiochemistry+of+Intramolecular+Schmidt+Reactions+en+Route+to+Bridged+Bicyclic+Lactams&rft.volume=129&rft.issue=10&rft.pages=2766-2767&rft.date=2007&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2596723%23id-name%3DPMC&rft_id=info%3Apmid%2F17302421&rft_id=info%3Adoi%2F10.1021%2Fja068919r&rft.au=Lei+Yao&rft.au=Jeffrey+Aub%C3%A9&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2596723&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASchmidt+reaction" 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="CITEREFWrobleskiSahasrabudheAubé2004" class="citation journal cs1">Wrobleski, Aaron; Sahasrabudhe, Kiran; Aubé, Jeffrey (May 2004). "Asymmetric Total Synthesis of Dendrobatid Alkaloids: Preparation of Indolizidine 251F and Its 3-Desmethyl Analogue Using an Intramolecular Schmidt Reaction Strategy". <i>Journal of the American Chemical Society</i>. <b>126</b> (17): 5475–5481. <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%2Fja0320018">10.1021/ja0320018</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/15113219">15113219</a>.</cite><span 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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 href="/wiki/Curtius_rearrangement" title="Curtius rearrangement">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 class="mw-selflink selflink">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> <!-- NewPP limit report Parsed by mw‐web.codfw.main‐f69cdc8f6‐4pcp9 Cached time: 20241122142646 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.477 seconds Real time usage: 1.157 seconds Preprocessor visited node count: 1216/1000000 Post‐expand include size: 141056/2097152 bytes Template argument size: 1704/2097152 bytes Highest expansion depth: 11/100 Expensive parser function count: 2/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 53609/5000000 bytes Lua time usage: 0.245/10.000 seconds Lua memory usage: 5210681/52428800 bytes Number of Wikibase entities loaded: 0/400 --> <!-- Transclusion expansion time report (%,ms,calls,template) 100.00% 981.787 1 -total 41.49% 407.311 4 Template:Navbox 40.69% 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