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Sommelet<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> and <a href="/wiki/Charles_R._Hauser" title="Charles R. Hauser">Charles R. Hauser</a><sup id="cite_ref-Hauser_2-0" class="reference"><a href="#cite_note-Hauser-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>) is a <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearrangement reaction</a> of certain <a href="/wiki/Benzyl" class="mw-redirect" title="Benzyl">benzyl</a> <a href="/wiki/Quaternary_ammonium_salt" class="mw-redirect" title="Quaternary ammonium salt">quaternary ammonium salts</a>.<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><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 reagent is <a href="/wiki/Sodium_amide" title="Sodium amide">sodium amide</a> or another alkali metal amide and the reaction product a <i>N</i>,<i>N</i>-dialkylbenzylamine with a new <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> group in the <a href="/wiki/Aromatic_ortho_position" class="mw-redirect" title="Aromatic ortho position">aromatic ortho position</a>. For example, benzyltrimethylammonium iodide, [(C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>)N(CH<sub>3</sub>)<sub>3</sub>]I, rearranges in the presence of sodium amide to yield the <i>o</i>-methyl derivative of <a href="/wiki/Dimethylbenzylamine" title="Dimethylbenzylamine"><i>N</i>,<i>N</i>-dimethylbenzylamine</a>.<sup id="cite_ref-Hauser_2-1" class="reference"><a href="#cite_note-Hauser-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:SommeletHauserReaction.svg" class="mw-file-description" title="Sommelet-Hauser rearrangement"><img alt="Sommelet-Hauser rearrangement" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/SommeletHauserReaction.svg/273px-SommeletHauserReaction.svg.png" decoding="async" width="273" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/SommeletHauserReaction.svg/410px-SommeletHauserReaction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/61/SommeletHauserReaction.svg/546px-SommeletHauserReaction.svg.png 2x" data-file-width="273" data-file-height="145" /></a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Mechanism">Mechanism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sommelet%E2%80%93Hauser_rearrangement&action=edit&section=1" title="Edit section: Mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The benzylic methylene proton is acidic and deprotonation takes place to produce the benzylic <a href="/wiki/Ylide" title="Ylide">ylide</a> (<b>1</b>). This ylide is in equilibrium with a second ylide that is formed by deprotonation of one of the ammonium methyl groups (<b>2</b>). Though the second ylide is present in much smaller amounts, it undergoes a <a href="/wiki/2,3-sigmatropic_rearrangement" title="2,3-sigmatropic rearrangement">2,3-sigmatropic rearrangement</a> because it is more reactive than the first one and subsequent aromatization to form the final product (<b>3</b>).<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Sommelet-Hauser_Rearrangement_Mechanism_V.png" class="mw-file-description" title="Sommelet-Hauser mechanism"><img alt="Sommelet-Hauser mechanism" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Sommelet-Hauser_Rearrangement_Mechanism_V.png/500px-Sommelet-Hauser_Rearrangement_Mechanism_V.png" decoding="async" width="500" height="284" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Sommelet-Hauser_Rearrangement_Mechanism_V.png/750px-Sommelet-Hauser_Rearrangement_Mechanism_V.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Sommelet-Hauser_Rearrangement_Mechanism_V.png/1000px-Sommelet-Hauser_Rearrangement_Mechanism_V.png 2x" data-file-width="4845" data-file-height="2755" /></a></span></dd></dl> <p>The <a href="/wiki/Stevens_rearrangement" title="Stevens rearrangement">Stevens rearrangement</a> is a competing reaction. </p> <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=Sommelet%E2%80%93Hauser_rearrangement&action=edit&section=2" 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"><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">M. Sommelet, Compt. Rend. 205, 56 (1937).</span> </li> <li id="cite_note-Hauser-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Hauser_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Hauser_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><i>Rearrangements of Benzyltrimethylammonium Ion and Related Quaternary Ammonium Ions by Sodium Amide Involving Migration into the Ring</i> Simon W. Kantor, Charles R. Hauser <a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a>, <b>1951</b>, 73 (9), pp 4122–4131 <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><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%2Fja01153a022">10.1021/ja01153a022</a></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarch,_Jerry1985" class="citation cs2"><a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (1985), <a rel="nofollow" class="external text" href="https://www.google.co.in/books/edition/_/ZKqWAQAACAAJ?hl=en"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition</i></a>, New York: Wiley, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471854722" title="Special:BookSources/9780471854722"><bdi>9780471854722</bdi></a>, <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/642506595">642506595</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure%2C+3rd+edition&rft.place=New+York&rft.pub=Wiley&rft.date=1985&rft_id=info%3Aoclcnum%2F642506595&rft.isbn=9780471854722&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fwww.google.co.in%2Fbooks%2Fedition%2F_%2FZKqWAQAACAAJ%3Fhl%3Den&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASommelet%E2%80%93Hauser+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a>, Coll. Vol. 4, p.585 (1963); Vol. 34, p.61 (1954) <a rel="nofollow" class="external text" href="http://orgsynth.org/orgsyn/pdfs/CV4P0585.pdf">Link</a>.</span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text">Ahluwalia, V. K., and R. K. Parashar. Organic Reaction Mechanisms. Harrow, U.K.: Alpha Science International, 2005. Print.</span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Sommelet–Hauser_rearrangement&oldid=1118576832">https://en.wikipedia.org/w/index.php?title=Sommelet–Hauser_rearrangement&oldid=1118576832</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Rearrangement_reactions" title="Category:Rearrangement reactions">Rearrangement reactions</a></li><li><a href="/wiki/Category:Name_reactions" title="Category:Name reactions">Name reactions</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 27 October 2022, at 19:38<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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