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<div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Nef_reaction" title="Nef reaction">Nef reaction</a> or <a href="/wiki/Nef_synthesis" title="Nef synthesis">Nef synthesis</a>.</div> <p>The <b>Nef isocyanide reaction</b> is an <a href="/wiki/Addition_reaction" title="Addition reaction">addition reaction</a> that takes place between <a href="/wiki/Isocyanide" title="Isocyanide">isocyanides</a> and <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chlorides</a> to form <a href="/wiki/Imidoyl_chloride" title="Imidoyl chloride">imidoyl chloride</a> products, a process first discovered by <a href="/wiki/John_Ulric_Nef_(chemist)" title="John Ulric Nef (chemist)">John Ulrich Nef</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-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Nef-isocyanide.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Nef-isocyanide.png/400px-Nef-isocyanide.png" decoding="async" width="400" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Nef-isocyanide.png/600px-Nef-isocyanide.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Nef-isocyanide.png/800px-Nef-isocyanide.png 2x" data-file-width="9678" data-file-height="1539" /></a><figcaption></figcaption></figure> <p>The product imidoyl chloride can be hydrolyzed to give the <a href="/wiki/Amide" title="Amide">amide</a>, trapped with other <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a>, or undergo halide abstraction with silver salts to form an acyl nitrilium intermediate.<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> </p><p>The reaction is of some theoretical interest, as kinetic measurements<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> and DFT studies<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> have indicated that the addition occurs in one step, without the intermediacy of a <a href="/wiki/Tetrahedral_intermediate" class="mw-redirect" title="Tetrahedral intermediate">tetrahedral intermediate</a> that is commonly proposed for carbonyl addition reactions. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nef_isocyanide_reaction&action=edit&section=1" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li> <li><a href="/wiki/Insertion_reaction" title="Insertion reaction">Insertion reaction</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=Nef_isocyanide_reaction&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"><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 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