Methylenation - Wikipedia

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<span>Methylenation adjacent to carbonyl groups</span> </div> </a> <ul id="toc-Methylenation_adjacent_to_carbonyl_groups-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_approaches" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_approaches"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Other approaches</span> </div> </a> <ul id="toc-Other_approaches-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav 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class="firstHeading mw-first-heading"><span class="mw-page-title-main">Methylenation</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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sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <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"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical reaction which adds a –CH2– group to a molecule</div> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>methylenation</b> is a <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> that inserts a <a href="/wiki/Methylene_group" title="Methylene group">methylene</a> (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>−</span>) group into a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a>: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {A-B}}\longrightarrow {\ce {A}}{\color {red}{\ce {-CH2 -}}}{\ce {B}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>A</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>B</mtext> </mrow> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <mtext>A</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </mrow> </mstyle> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>B</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {A-B}}\longrightarrow {\ce {A}}{\color {red}{\ce {-CH2 -}}}{\ce {B}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/27233668b0ef7d494c066aaf41619ae493d118fb" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:21.773ex; height:2.843ex;" alt="{\displaystyle {\ce {A-B}}\longrightarrow {\ce {A}}{\color {red}{\ce {-CH2 -}}}{\ce {B}}}"></span></dd></dl> <p>In a related sense, it also describes a process in which a divalent group of a starting material is removed and replaced with a terminal CH<sub>2</sub> group: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {A=E}}\longrightarrow {\ce {A}}{\color {red}{\ce {=CH2}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>A</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>E</mtext> </mrow> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <mtext>A</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {A=E}}\longrightarrow {\ce {A}}{\color {red}{\ce {=CH2}}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/cbe2203fae31d163dc7341294969bce677f9ac4a" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:18.257ex; height:2.843ex;" alt="{\displaystyle {\ce {A=E}}\longrightarrow {\ce {A}}{\color {red}{\ce {=CH2}}}}"></span></dd></dl> <p>Methylenation in this context is also known as <b>methenylation</b>. Most commonly, E is an oxygen atom, so that the reaction results in terminal <a href="/wiki/Alkene" title="Alkene">alkenes</a> from <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> and <a href="/wiki/Ketone" title="Ketone">ketones</a>, or more rarely, <a href="/wiki/Enol_ether" title="Enol ether">enol ethers</a> from <a href="/wiki/Ester" title="Ester">esters</a> or <a href="/wiki/Enamine" title="Enamine">enamines</a> from <a href="/wiki/Amide" title="Amide">amides</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Methods">Methods</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylenation&action=edit&section=1" title="Edit section: Methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Methylene_Insertion_into_Alkanes">Methylene Insertion into Alkanes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylenation&action=edit&section=2" title="Edit section: Methylene Insertion into Alkanes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Singlet methylene</a> (<sup>1</sup>[:CH<sub>2</sub>]), produced from photolysis of <a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a> under ultraviolet irradiation,<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> methylenates hydrocarbons. Arenes and olefins undergo methylenation to give cyclopropanated products. In the case of arenes, the cyclopropanation product undergoes further electrocyclic ring opening to give cycloheptatriene products (<a href="/wiki/Buchner_ring_expansion" title="Buchner ring expansion">Buchner ring expansion</a>).<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> Alkenes undergo both C=C methylenation and C–H methylenation insertion to give a mixture of cyclopropanation and <a href="/wiki/Homologation_reaction" title="Homologation reaction">homologation</a> products. </p><p>Reflecting the exceptionally high reactivity of singlet methylene, normally unreactive alkanes undergo methylenation to give homologation products, even at –75 °C.<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> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {R-H}}+{\color {red}{\ce {CH2}}}\longrightarrow {\ce {R}}{\color {red}{\ce {-CH2}}}{\ce {H}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>H</mtext> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <mtext>R</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>H</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {R-H}}+{\color {red}{\ce {CH2}}}\longrightarrow {\ce {R}}{\color {red}{\ce {-CH2}}}{\ce {H}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/9f75b246881d4063ce440c33ece559d8449b86e2" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:27.411ex; height:2.843ex;" alt="{\displaystyle {\ce {R-H}}+{\color {red}{\ce {CH2}}}\longrightarrow {\ce {R}}{\color {red}{\ce {-CH2}}}{\ce {H}}}"></span></dd></dl><p> Photolysis of a solution of diazomethane in <i>n-</i>pentane gives a mixture of hexanes and higher homologues. At –75 °C, the product ratio is 48:35:17 mixture of <i>n</i>-hexane, 2-methylpentane, and 3-methylpentane. The ratio is remarkably close to the statistical product ratio of 6:4:2 (~50:33:17) based on the number of available C–H bonds at each position that could undergo methylene insertion. As a result, <a href="/wiki/William_von_Eggers_Doering" title="William von Eggers Doering">Doering</a> and coworkers concluded:</p><blockquote><p><i>Methylene must be classed as the most indiscriminate reagent known in organic chemistry.</i></p></blockquote> <div class="mw-heading mw-heading3"><h3 id="Methylene-for-oxo_reactions">Methylene-for-oxo reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylenation&action=edit&section=3" title="Edit section: Methylene-for-oxo reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A common method for methylenation involves the <a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a> using <a href="/wiki/Methylenetriphenylphosphorane" title="Methylenetriphenylphosphorane">methylenetriphenylphosphorane</a> with an aldehyde (Ph = <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub></span>):<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> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {RCHO + Ph3P=CH2 -> RCH=CH2 + Ph3PO}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>RCHO</mtext> <mo>+</mo> <msubsup> <mtext>Ph</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>P</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <mtext>RCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>Ph</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>PO</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RCHO + Ph3P=CH2 -> RCH=CH2 + Ph3PO}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/7a34fa3756dbbce6b7592fb02301888fc4c02ee8" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:48.248ex; height:2.843ex;" alt="{\displaystyle {\ce {RCHO + Ph3P=CH2 -> RCH=CH2 + Ph3PO}}}"></span></dd></dl> <p>A related reaction can be accomplished with <a href="/wiki/Tebbe%27s_reagent" title="Tebbe's reagent">Tebbe's reagent</a>, which is sufficiently versatile to allow methylenation of <a href="/wiki/Ester" title="Ester">esters</a>:<sup id="cite_ref-Strauss_5-0" class="reference"><a href="#cite_note-Strauss-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {RCO2R' + Cp2Ti(Cl)CH2AlMe2 -> RC(OR')=CH2 + Cp2TiOAlMe2Cl}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>RCO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mo>+</mo> <msubsup> <mtext>Cp</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>Ti</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>Cl</mtext> <mo stretchy="false">)</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>AlMe</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <mtext>RC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msup> <mtext>OR</mtext> <mo>′</mo> </msup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>Cp</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>TiOAlMe</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>Cl</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RCO2R' + Cp2Ti(Cl)CH2AlMe2 -> RC(OR')=CH2 + Cp2TiOAlMe2Cl}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/a5307c467d0f82dd3213df2ad1518b699dc39d34" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:73.765ex; height:3.176ex;" alt="{\displaystyle {\ce {RCO2R' + Cp2Ti(Cl)CH2AlMe2 -> RC(OR')=CH2 + Cp2TiOAlMe2Cl}}}"></span></dd></dl> <p>Other less well-defined titanium reagents, e.g., <a href="/wiki/Lombardo_methylenation" title="Lombardo methylenation">Lombardo's reagent</a>, effect similar transformations.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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:LombardoReagent.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/98/LombardoReagent.png/400px-LombardoReagent.png" decoding="async" width="400" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/98/LombardoReagent.png/600px-LombardoReagent.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/98/LombardoReagent.png/800px-LombardoReagent.png 2x" data-file-width="982" data-file-height="230" /></a></span></dd></dl> <p>Carbanions derived from methylsulfones have also been employed, equivalently to the Wittig reaction.<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> <div class="mw-heading mw-heading3"><h3 id="Methylenation_adjacent_to_carbonyl_groups">Methylenation adjacent to carbonyl groups</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylenation&action=edit&section=4" title="Edit section: Methylenation adjacent to carbonyl groups"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketones and esters can be methylenated at the α position to give α,β-unsaturated carbonyl products containing an additional terminal CH<sub>2</sub> group in a three-step process known as the <b><a href="/wiki/Albert_Eschenmoser" title="Albert Eschenmoser">Eschenmoser</a> methylenation</b>.<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> An <a href="/wiki/Enolate" title="Enolate">enolate</a> is generated by deprotonation of the α-C–H bond using a hindered lithium amide (LiNR<sub>2</sub>) base (e.g., <a href="/wiki/Lithium_diisopropylamide" title="Lithium diisopropylamide">LDA</a>, <a href="/wiki/Lithium_bis(trimethylsilyl)amide" title="Lithium bis(trimethylsilyl)amide">LHMDS</a>). Subsequently, the enolate is reacted with <a href="/wiki/Eschenmoser%27s_salt" title="Eschenmoser's salt">Eschenmoser's salt</a> ([Me<sub>2</sub>N=CH<sub>2</sub>]<sup>+</sup>I<sup>–</sup>) to give a β-dimethylamino carbonyl compound (<a href="/wiki/Mannich_base" title="Mannich base">Mannich base</a>). The Mannich base is then subjected to methylation or N-oxidation to give a <a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">trimethylammonium salt</a> or <a href="/wiki/Amine_oxide" title="Amine oxide">amine <i>N</i>-oxide</a>, which is then subjected to <a href="/wiki/Hofmann_elimination" title="Hofmann elimination">Hofmann elimination</a> or <a href="/wiki/Cope_reaction" title="Cope reaction">Cope elimination</a>, respectively to give the α-methylene carbonyl compound. If the Hofmann elimination is used, the process can be represented as follows: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {RC(=O)CH2R' -> RC(=O) CH(CH2NMe2)R' -> [RC(=O) CH(CH2NMe3)R']+I- -> RC(=O) C(=CH2)(R')}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>RC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mo stretchy="false">⟶</mo> <mtext>RC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>NMe</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mo stretchy="false">⟶</mo> <msup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>RC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>NMe</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mo stretchy="false">]</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> <msup> <mtext>I</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> <mo stretchy="false">⟶</mo> <mtext>RC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mo stretchy="false">)</mo> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RC(=O)CH2R' -> RC(=O) CH(CH2NMe2)R' -> [RC(=O) CH(CH2NMe3)R']+I- -> RC(=O) C(=CH2)(R')}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/83dcb1ac6884d2821a7d7ea6e677d59ef397ca7c" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:112.67ex; height:3.509ex;" alt="{\displaystyle {\ce {RC(=O)CH2R' -> RC(=O) CH(CH2NMe2)R' -> [RC(=O) CH(CH2NMe3)R']+I- -> RC(=O) C(=CH2)(R')}}}"></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Other_approaches">Other approaches</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylenation&action=edit&section=5" title="Edit section: Other approaches"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Ethenolysis" title="Ethenolysis">Ethenolysis</a> is a method for methylenation of internal alkene as illustrated by the following example: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {RCH=CHR}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\ce {2 RCH=}}{\color {red}{\ce {CH2}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>RCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>CHR</mtext> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace" /> <mtext>RCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RCH=CHR}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\ce {2 RCH=}}{\color {red}{\ce {CH2}}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/36f3d612a488f9f8cff38e0215966d9a674b8eaa" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:43.732ex; height:2.843ex;" alt="{\displaystyle {\ce {RCH=CHR}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\ce {2 RCH=}}{\color {red}{\ce {CH2}}}}"></span></dd></dl> <p>In principle, the addition of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub></span> across a <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C=C</span> double bond could be classified as a methylenation, but such transformations are commonly described as <a href="/wiki/Cyclopropanation" title="Cyclopropanation">cyclopropanations</a>. </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=Methylenation&action=edit&section=6" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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 .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="CITEREFBraunBassPilling1970" class="citation journal cs1">Braun, W.; 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Methylenation - Wikipedia