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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Newman–Kwart rearrangement</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><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">Newman-Kwart rearrangement </th></tr> <tr> <td>Named after </td> <td><a href="/wiki/Melvin_Spencer_Newman" title="Melvin Spencer Newman">Melvin Spencer Newman</a> <br /> Harold Kwart </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/newman-kwart-rearrangement.shtm">newman-kwart-rearrangement</a></span> </td></tr> <tr> <td><a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">RSC</a> ontology ID </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/ols/ontologies/rxno/terms?iri=http%3A%2F%2Fpurl.obolibrary.org%2Fobo%2FRXNO_0000412">RXNO:0000412</a></span> </td></tr> <tr> <td style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2"> </td></tr> </tbody></table> <p>The <b>Newman–Kwart rearrangement</b> is a type of <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearrangement reaction</a> in which the <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl group</a> of an <a href="/wiki/Thiocarbamate" title="Thiocarbamate"><i>O</i>-aryl thiocarbamate</a>, ArOC(=S)NMe<sub>2</sub>, <a href="/wiki/Migration_(chemistry)" class="mw-redirect" title="Migration (chemistry)">migrates</a> from the <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> atom to the <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> atom, forming an <i>S</i>-aryl thiocarbamate, ArSC(=O)NMe<sub>2</sub>.<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-:0_2-0" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Renny2008_3-0" class="reference"><a href="#cite_note-Renny2008-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The reaction is named after its discoverers, <a href="/wiki/Melvin_Spencer_Newman" title="Melvin Spencer Newman">Melvin Spencer Newman</a><sup id="cite_ref-Newman_4-0" class="reference"><a href="#cite_note-Newman-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and Harold Kwart.<sup id="cite_ref-Kwart_5-0" class="reference"><a href="#cite_note-Kwart-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The reaction is a manifestation of the <a href="/wiki/Double_bond_rule" title="Double bond rule">double bond rule</a>. The Newman–Kwart reaction represents a useful synthetic tool for the preparation of <a href="/wiki/Thiophenol" title="Thiophenol">thiophenol</a> derivatives. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Newman-Kwart-rearrangement-general.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Newman-Kwart-rearrangement-general.png/400px-Newman-Kwart-rearrangement-general.png" decoding="async" width="400" height="79" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Newman-Kwart-rearrangement-general.png/600px-Newman-Kwart-rearrangement-general.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Newman-Kwart-rearrangement-general.png/800px-Newman-Kwart-rearrangement-general.png 2x" data-file-width="2150" data-file-height="427" /></a></span></dd></dl> <meta property="mw:PageProp/toc" /> <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=Newman%E2%80%93Kwart_rearrangement&action=edit&section=1" title="Edit section: Mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Newman–Kwart rearrangement is <a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">intramolecular</a>. It is generally believed to be a concerted process, proceeding <i>via</i> a four-membered cyclic <a href="/wiki/Transition_state" title="Transition state">transition state</a> (rather than a two-step process passing through a discrete <a href="/wiki/Reaction_intermediate" title="Reaction intermediate">reactive intermediate</a>).<sup id="cite_ref-Renny2008_3-1" class="reference"><a href="#cite_note-Renny2008-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Renny2010_6-0" class="reference"><a href="#cite_note-Renny2010-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The enthalpy of activation for this transition state is generally quite high for typical substrates (Δ<i>H</i><sup>‡</sup> ~ 30 to 40 kcal/mol), necessitating high reaction temperatures (200 to 300 °C, Ph<sub>2</sub>O as solvent or heat).<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> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:NKR-mechanism-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/NKR-mechanism-2D-skeletal.png/700px-NKR-mechanism-2D-skeletal.png" decoding="async" width="700" height="289" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/NKR-mechanism-2D-skeletal.png/1050px-NKR-mechanism-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e1/NKR-mechanism-2D-skeletal.png/1400px-NKR-mechanism-2D-skeletal.png 2x" data-file-width="2000" data-file-height="826" /></a></span></dd></dl> <p>A Pd-catalyzed process<sup id="cite_ref-:0_2-1" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and conditions under photoredox catalysis<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> (both proceeding through complex multistep mechanisms) are known. These catalytic processes allow for much milder reaction conditions to be used (100 °C for Pd catalysis, ambient temperature for photoredox). </p> <div class="mw-heading mw-heading2"><h2 id="Use_for_preparation_of_thiophenols">Use for preparation of thiophenols</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Newman%E2%80%93Kwart_rearrangement&action=edit&section=2" title="Edit section: Use for preparation of thiophenols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Newman–Kwart rearrangement is an important prelude to the synthesis of <a href="/wiki/Thiophenols" class="mw-redirect" title="Thiophenols">thiophenols</a>. A <a href="/wiki/Phenol" title="Phenol">phenol</a> (<b>1</b>) is deprotonated with a base followed by treatment with a <a href="/wiki/Thiocarbamoyl_chloride" class="mw-redirect" title="Thiocarbamoyl chloride">thiocarbamoyl chloride</a> (<b>2</b>) to form an <i>O</i>-aryl thiocarbamate (<b>3</b>). Heating <b>3</b> to around 250 °C causes it undergo Newman–Kwart rearrangement to an <i>S</i>-aryl <a href="/wiki/Thiocarbamate" title="Thiocarbamate">thiocarbamate</a> (<b>4</b>). Alkaline hydrolysis or similar cleavage yields a thiophenol (<b>5</b>).<sup id="cite_ref-Renny2010_6-1" class="reference"><a href="#cite_note-Renny2010-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Phenols-to-thiophenols-via-NKR-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Phenols-to-thiophenols-via-NKR-2D-skeletal.svg/900px-Phenols-to-thiophenols-via-NKR-2D-skeletal.svg.png" decoding="async" width="900" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Phenols-to-thiophenols-via-NKR-2D-skeletal.svg/1350px-Phenols-to-thiophenols-via-NKR-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Phenols-to-thiophenols-via-NKR-2D-skeletal.svg/1800px-Phenols-to-thiophenols-via-NKR-2D-skeletal.svg.png 2x" data-file-width="2000" data-file-height="311" /></a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Newman%E2%80%93Kwart_rearrangement&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/Smiles_rearrangement" title="Smiles rearrangement">Smiles rearrangement</a></li> <li><a href="/wiki/Chapman_rearrangement" class="mw-redirect" title="Chapman rearrangement">Chapman 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=Newman%E2%80%93Kwart_rearrangement&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"><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 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Springer Berlin / Heidelberg. pp. 131–161. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F128_065">10.1007/128_065</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-68099-4" title="Special:BookSources/978-3-540-68099-4"><bdi>978-3-540-68099-4</bdi></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/0340-1022">0340-1022</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/23605512">23605512</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Thione%E2%80%93Thiol+Rearrangement%3A+Miyazaki%E2%80%93Newman%E2%80%93Kwart+Rearrangement+and+Others&rft.series=Topics+in+Current+Chemistry&rft.pages=131-161&rft.pub=Springer+Berlin+%2F+Heidelberg&rft.date=2007&rft_id=info%3Adoi%2F10.1007%2F128_065&rft.issn=0340-1022&rft_id=info%3Apmid%2F23605512&rft.isbn=978-3-540-68099-4&rft.aulast=Zonta&rft.aufirst=C.&rft.au=De+Lucchi%2C+O.&rft.au=Volpicelli%2C+R.&rft.au=Cotarca%2C+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANewman%E2%80%93Kwart+rearrangement" class="Z3988"></span></span> </li> <li id="cite_note-:0-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_2-1"><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="CITEREFHarveyJoverLloyd-JonesMoseley2009" class="citation journal cs1">Harvey, J. 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Newman; Frederick W. Hetzel (1971). "Thiophenols from Phenols: <a href="/wiki/2-Naphthalenethiol" title="2-Naphthalenethiol">2-Naphthalenethiol</a>". <i>Org. Synth</i>. <b>51</b>: 139. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.051.0139">10.15227/orgsyn.051.0139</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Org.+Synth.&rft.atitle=Thiophenols+from+Phenols%3A+2-Naphthalenethiol&rft.volume=51&rft.pages=139&rft.date=1971&rft_id=info%3Adoi%2F10.15227%2Forgsyn.051.0139&rft.au=Melvin+S.+Newman&rft.au=Frederick+W.+Hetzel&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANewman%E2%80%93Kwart+rearrangement" class="Z3988"></span></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=Newman–Kwart_rearrangement&oldid=1247917260">https://en.wikipedia.org/w/index.php?title=Newman–Kwart_rearrangement&oldid=1247917260</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 26 September 2024, at 18:41<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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