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id="toc-Classifications-sublist" class="vector-toc-list"> <li id="toc-Acryloyl_group" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acryloyl_group"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Acryloyl group</span> </div> </a> <ul id="toc-Acryloyl_group-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-α,β-Unsaturated_acids,_esters,_and_amides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#α,β-Unsaturated_acids,_esters,_and_amides"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>α,β-Unsaturated acids, esters, and amides</span> </div> </a> <ul id="toc-α,β-Unsaturated_acids,_esters,_and_amides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Enones" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Enones"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Enones</span> </div> </a> <ul id="toc-Enones-sublist" class="vector-toc-list"> <li id="toc-Cyclic_enones" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cyclic_enones"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3.1</span> <span>Cyclic enones</span> </div> </a> <ul id="toc-Cyclic_enones-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Enals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Enals"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Enals</span> </div> </a> <ul id="toc-Enals-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions_of_α,β-unsaturated_carbonyls" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions_of_α,β-unsaturated_carbonyls"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Reactions of α,β-unsaturated carbonyls</span> </div> </a> <ul id="toc-Reactions_of_α,β-unsaturated_carbonyls-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-α,β-Unsaturated_thioesters" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#α,β-Unsaturated_thioesters"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>α,β-Unsaturated thioesters</span> </div> </a> <ul id="toc-α,β-Unsaturated_thioesters-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </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">6</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 aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox 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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">Functional group of organic compounds</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:%CE%91,%CE%B2-unsaturated_labeled.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/%CE%91%2C%CE%B2-unsaturated_labeled.svg/220px-%CE%91%2C%CE%B2-unsaturated_labeled.svg.png" decoding="async" width="220" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/%CE%91%2C%CE%B2-unsaturated_labeled.svg/330px-%CE%91%2C%CE%B2-unsaturated_labeled.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5b/%CE%91%2C%CE%B2-unsaturated_labeled.svg/440px-%CE%91%2C%CE%B2-unsaturated_labeled.svg.png 2x" data-file-width="330" data-file-height="233" /></a><figcaption>General structure of α,β-unsaturated carbonyl compounds. R<sub>2</sub> and R<sub>4</sub> can also be single hydrogens.</figcaption></figure> <p><b>α,β-Unsaturated carbonyl compounds</b> are <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> with the general structure (O=CR)−C<sup>α</sup>=C<sup>β</sup>−R.<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> Such compounds include <a href="/wiki/Enone" class="mw-redirect" title="Enone">enones</a> and <a href="/wiki/Enal" class="mw-redirect" title="Enal">enals</a>, but also carboxylic acids and the corresponding esters and amides. In these compounds, the <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl group</a> is <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated</a> with an <a href="/wiki/Alkene" title="Alkene">alkene</a> (hence the adjective <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">unsaturated</a>). Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β-carbon. This pattern of reactivity is called <a href="/wiki/Vinylogous" class="mw-redirect" title="Vinylogous">vinylogous</a>. Examples of unsaturated carbonyls are <a href="/wiki/Acrolein" title="Acrolein">acrolein</a> (propenal), <a href="/wiki/Mesityl_oxide" title="Mesityl oxide">mesityl oxide</a>, <a href="/wiki/Acrylic_acid" title="Acrylic acid">acrylic acid</a>, and <a href="/wiki/Maleic_acid" title="Maleic acid">maleic acid</a>. Unsaturated carbonyls can be prepared in the laboratory in an <a href="/wiki/Aldol_reaction" title="Aldol reaction">aldol reaction</a> and in the <a href="/wiki/Perkin_reaction" title="Perkin reaction">Perkin reaction</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Classifications">Classifications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91,%CE%B2-Unsaturated_carbonyl_compound&action=edit&section=1" title="Edit section: Classifications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>α,β-Unsaturated carbonyl compounds can be subclassified according to the nature of the carbonyl and alkene groups. </p> <ul class="gallery mw-gallery-traditional skin-invert-image"> <li class="gallerycaption">Parent α,β-unsaturated carbonyls</li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Methyl_vinyl_ketone.svg" class="mw-file-description" title="Methyl vinyl ketone, the simplest α,β-unsaturated ketone"><img alt="Methyl vinyl ketone, the simplest α,β-unsaturated ketone" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Methyl_vinyl_ketone.svg/120px-Methyl_vinyl_ketone.svg.png" decoding="async" width="120" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Methyl_vinyl_ketone.svg/180px-Methyl_vinyl_ketone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Methyl_vinyl_ketone.svg/240px-Methyl_vinyl_ketone.svg.png 2x" data-file-width="210" data-file-height="150" /></a></span></div> <div class="gallerytext"><a href="/wiki/Methyl_vinyl_ketone" title="Methyl vinyl ketone">Methyl vinyl ketone</a>, the simplest α,β-unsaturated ketone</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Acrolein-2D-skeletal-plus-H.png" class="mw-file-description" title="Acrolein, the simplest α,β-unsaturated aldehyde"><img alt="Acrolein, the simplest α,β-unsaturated aldehyde" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Acrolein-2D-skeletal-plus-H.png/120px-Acrolein-2D-skeletal-plus-H.png" decoding="async" width="120" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Acrolein-2D-skeletal-plus-H.png/180px-Acrolein-2D-skeletal-plus-H.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Acrolein-2D-skeletal-plus-H.png/240px-Acrolein-2D-skeletal-plus-H.png 2x" data-file-width="1100" data-file-height="802" /></a></span></div> <div class="gallerytext"><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a>, the simplest α,β-unsaturated aldehyde</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Methylacrylat.svg" class="mw-file-description" title="Methyl acrylate, an α,β-unsaturated ester"><img alt="Methyl acrylate, an α,β-unsaturated ester" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Methylacrylat.svg/120px-Methylacrylat.svg.png" decoding="async" width="120" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Methylacrylat.svg/180px-Methylacrylat.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/23/Methylacrylat.svg/240px-Methylacrylat.svg.png 2x" data-file-width="179" data-file-height="103" /></a></span></div> <div class="gallerytext"><a href="/wiki/Methyl_acrylate" title="Methyl acrylate">Methyl acrylate</a>, an α,β-unsaturated ester</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Acrylamide-2D-skeletal.png" class="mw-file-description" title="Acrylamide, precursor to polyacrylamide"><img alt="Acrylamide, precursor to polyacrylamide" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Acrylamide-2D-skeletal.png/120px-Acrylamide-2D-skeletal.png" decoding="async" width="120" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Acrylamide-2D-skeletal.png/180px-Acrylamide-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/01/Acrylamide-2D-skeletal.png/240px-Acrylamide-2D-skeletal.png 2x" data-file-width="1100" data-file-height="693" /></a></span></div> <div class="gallerytext"><a href="/wiki/Acrylamide" title="Acrylamide">Acrylamide</a>, precursor to polyacrylamide</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Maleins%C3%A4ure.svg" class="mw-file-description" title="Maleic acid, an α,β-unsaturated dicarbonyl"><img alt="Maleic acid, an α,β-unsaturated dicarbonyl" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Maleins%C3%A4ure.svg/120px-Maleins%C3%A4ure.svg.png" decoding="async" width="120" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Maleins%C3%A4ure.svg/180px-Maleins%C3%A4ure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Maleins%C3%A4ure.svg/240px-Maleins%C3%A4ure.svg.png 2x" data-file-width="187" data-file-height="97" /></a></span></div> <div class="gallerytext"><a href="/wiki/Maleic_acid" title="Maleic acid">Maleic acid</a>, an α,β-unsaturated <i>di</i>carbonyl</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Fumaric-acid-2D-skeletal.png" class="mw-file-description" title="Fumaric acid, isomeric with maleic acid"><img alt="Fumaric acid, isomeric with maleic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Fumaric-acid-2D-skeletal.png/120px-Fumaric-acid-2D-skeletal.png" decoding="async" width="120" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Fumaric-acid-2D-skeletal.png/180px-Fumaric-acid-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Fumaric-acid-2D-skeletal.png/240px-Fumaric-acid-2D-skeletal.png 2x" data-file-width="1100" data-file-height="627" /></a></span></div> <div class="gallerytext"><a href="/wiki/Fumaric_acid" title="Fumaric acid">Fumaric acid</a>, isomeric with maleic acid</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Acryloyl_chloride2.png" class="mw-file-description" title="Acryloyl chloride"><img alt="Acryloyl chloride" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Acryloyl_chloride2.png/120px-Acryloyl_chloride2.png" decoding="async" width="120" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Acryloyl_chloride2.png/180px-Acryloyl_chloride2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Acryloyl_chloride2.png/240px-Acryloyl_chloride2.png 2x" data-file-width="921" data-file-height="620" /></a></span></div> <div class="gallerytext"><a href="/wiki/Acryloyl_chloride" title="Acryloyl chloride">Acryloyl chloride</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:1,3-Diphenylprophene-2-one.svg" class="mw-file-description" title="Chalcone"><img alt="Chalcone" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/1%2C3-Diphenylprophene-2-one.svg/120px-1%2C3-Diphenylprophene-2-one.svg.png" decoding="async" width="120" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/1%2C3-Diphenylprophene-2-one.svg/180px-1%2C3-Diphenylprophene-2-one.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/1%2C3-Diphenylprophene-2-one.svg/240px-1%2C3-Diphenylprophene-2-one.svg.png 2x" data-file-width="1104" data-file-height="569" /></a></span></div> <div class="gallerytext"><a href="/wiki/Chalcone" title="Chalcone">Chalcone</a></div> </li> </ul> <div class="mw-heading mw-heading3"><h3 id="Acryloyl_group">Acryloyl group</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91,%CE%B2-Unsaturated_carbonyl_compound&action=edit&section=2" title="Edit section: Acryloyl group"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right skin-invert" typeof="mw:File/Thumb"><a href="/wiki/File:Acrylgruppe.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Acrylgruppe.svg/200px-Acrylgruppe.svg.png" decoding="async" width="200" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Acrylgruppe.svg/300px-Acrylgruppe.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Acrylgruppe.svg/400px-Acrylgruppe.svg.png 2x" data-file-width="144" data-file-height="77" /></a><figcaption>Structure of the acryloyl group</figcaption></figure> <p>α,β-Unsaturated carbonyl compounds featuring a carbonyl conjugated to an alkene that is terminal, or <a href="/wiki/Vinylic" class="mw-redirect" title="Vinylic">vinylic</a>, contain the <b>acryloyl group</b> (<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"><a href="/wiki/Hydrogen" title="Hydrogen">H</a><sub class="template-chem2-sub">2</sub><a href="/wiki/Carbon" title="Carbon">C</a>=CH−C(=<a href="/wiki/Oxygen" title="Oxygen">O</a>)−</span>); it is the <a href="/wiki/Acyl" class="mw-redirect" title="Acyl">acyl</a> group derived from <a href="/wiki/Acrylic_acid" title="Acrylic acid">acrylic acid</a>. The <a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">preferred IUPAC name</a> for the group is <b>prop-2-enoyl</b>, and it is also known as <b>acrylyl</b> or simply (and incorrectly) as <b>acryl</b>. Compounds containing an acryloyl group can be referred to as "acrylic compounds". </p> <div class="mw-heading mw-heading3"><h3 id="α,β-Unsaturated_acids,_esters,_and_amides"><span id=".CE.B1.2C.CE.B2-Unsaturated_acids.2C_esters.2C_and_amides"></span>α,β-Unsaturated acids, esters, and amides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91,%CE%B2-Unsaturated_carbonyl_compound&action=edit&section=3" title="Edit section: α,β-Unsaturated acids, esters, and amides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An <b>α,β-unsaturated acid</b> is a type of α,β-unsaturated carbonyl compound that consists of an <a href="/wiki/Alkene" title="Alkene">alkene</a> <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated</a> to a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>.<sup id="cite_ref-March_3-0" class="reference"><a href="#cite_note-March-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The simplest example is acrylic acid (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>=CHCO<sub class="template-chem2-sub">2</sub>H</span>). These compounds are prone to polymerization, giving rise to the large area of <a href="/wiki/Polyacrylate" class="mw-redirect" title="Polyacrylate">polyacrylate</a> plastics. <a href="/wiki/Acrylate_polymer" title="Acrylate polymer">Acrylate polymers</a> are derived from but do not contain the acrylate group.<sup id="cite_ref-Ullmann_4-0" class="reference"><a href="#cite_note-Ullmann-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The carboxyl group of acrylic acid can react with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> to form <a href="/wiki/Acrylamide" title="Acrylamide">acrylamide</a>, or with an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> to form an acrylate <a href="/wiki/Ester" title="Ester">ester</a>. Acrylamide and <a href="/wiki/Methyl_acrylate" title="Methyl acrylate">methyl acrylate</a> are commercially important examples of α,β-unsaturated <a href="/wiki/Amide" title="Amide">amides</a> and α,β-unsaturated esters, respectively. They also polymerize readily. Acrylic acid, its esters, and its amide derivatives feature the acryloyl group. </p><p>α,β-Unsaturated <a href="/wiki/Dicarbonyls" class="mw-redirect" title="Dicarbonyls">dicarbonyls</a> are also common. The parent compounds are <a href="/wiki/Maleic_acid" title="Maleic acid">maleic acid</a> and the isomeric <a href="/wiki/Fumaric_acid" title="Fumaric acid">fumaric acid</a>. Maleic acid forms esters, an imide, and an anhydride, i.e. <a href="/wiki/Diethyl_maleate" title="Diethyl maleate">diethyl maleate</a>, <a href="/wiki/Maleimide" title="Maleimide">maleimide</a>, and <a href="/wiki/Maleic_anhydride" title="Maleic anhydride">maleic anhydride</a>. Fumaric acid, as fumarate, is an intermediate in the <a href="/wiki/Krebs_citric_acid_cycle" class="mw-redirect" title="Krebs citric acid cycle">Krebs citric acid cycle</a>, which is of great importance in bioenergy. </p> <div class="mw-heading mw-heading3"><h3 id="Enones">Enones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91,%CE%B2-Unsaturated_carbonyl_compound&action=edit&section=4" title="Edit section: Enones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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">"Enone" redirects here. For the character in Greek mythology, see <a href="/wiki/Oenone" title="Oenone">Oenone</a>. For enone biomolecules used in paleothermometry, see <a href="/wiki/Alkenone" title="Alkenone">Alkenone</a>.</div> <p>An <b>enone</b> (or <b>alkenone</b>) is an organic compound containing both <a href="/wiki/Alkene" title="Alkene">alkene</a> and <a href="/wiki/Ketone" title="Ketone">ketone</a> functional groups. In an α,β-unsaturated enone, the alkene is <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated</a> to the carbonyl group of the ketone.<sup id="cite_ref-March_3-1" class="reference"><a href="#cite_note-March-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The simplest enone is <a href="/wiki/Methyl_vinyl_ketone" title="Methyl vinyl ketone">methyl vinyl ketone</a> (butenone, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>=CHCOCH<sub class="template-chem2-sub">3</sub></span>). Enones are typically produced using an <a href="/wiki/Aldol_condensation" title="Aldol condensation">aldol condensation</a> or <a href="/wiki/Knoevenagel_condensation" title="Knoevenagel condensation">Knoevenagel condensation</a>. Some commercially significant enones produced by condensations of <a href="/wiki/Acetone" title="Acetone">acetone</a> are <a href="/wiki/Mesityl_oxide" title="Mesityl oxide">mesityl oxide</a> (<a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimer</a> of acetone) and <a href="/wiki/Phorone" title="Phorone">phorone</a> and <a href="/wiki/Isophorone" title="Isophorone">isophorone</a> (<a href="/wiki/Trimer_(chemistry)" title="Trimer (chemistry)">trimers</a>).<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> In the <a href="/wiki/Meyer%E2%80%93Schuster_rearrangement" title="Meyer–Schuster rearrangement">Meyer–Schuster rearrangement</a>, the starting compound is a <a href="/wiki/Propargyl" class="mw-redirect" title="Propargyl">propargyl</a> <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>. Another method to access α,β-unsaturated carbonyls is via <a href="/wiki/Selenoxide_elimination" title="Selenoxide elimination">selenoxide elimination</a>. Cyclic enones can be prepared via the <a href="/wiki/Pauson%E2%80%93Khand_reaction" title="Pauson–Khand reaction">Pauson–Khand reaction</a>. </p> <figure class="mw-halign-center skin-invert" typeof="mw:File/Thumb"><a href="/wiki/File:Condensationaldolique.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Condensationaldolique.png/600px-Condensationaldolique.png" decoding="async" width="600" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Condensationaldolique.png/900px-Condensationaldolique.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/87/Condensationaldolique.png/1200px-Condensationaldolique.png 2x" data-file-width="1777" data-file-height="279" /></a><figcaption>General reaction for an aldol condensation between two carbonyl compounds</figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Cyclic_enones">Cyclic enones</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91,%CE%B2-Unsaturated_carbonyl_compound&action=edit&section=5" title="Edit section: Cyclic enones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The cyclic enones include <a href="/wiki/Cyclopropenone" title="Cyclopropenone">cyclopropenone</a>, cyclobutenone,<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> <a href="/wiki/Cyclopentenone" title="Cyclopentenone">cyclopentenone</a>, <a href="/wiki/Cyclohexenone" title="Cyclohexenone">cyclohexenone</a>, and cycloheptenone.<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> <div class="mw-heading mw-heading3"><h3 id="Enals">Enals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91,%CE%B2-Unsaturated_carbonyl_compound&action=edit&section=6" title="Edit section: Enals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An <b>enal</b> (or <b>alkenal</b>) is an organic compound containing both <a href="/wiki/Alkene" title="Alkene">alkene</a> and <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> functional groups. In an α,β-unsaturated enal, the alkene is <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated</a> to the carbonyl group of the aldehyde (formyl group).<sup id="cite_ref-March_3-2" class="reference"><a href="#cite_note-March-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The simplest enal is <a href="/wiki/Acrolein" title="Acrolein">acrolein</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>=CHCHO</span>). Other examples include <a href="/wiki/Cis-3-Hexenal" title="Cis-3-Hexenal"><i>cis</i>-3-hexenal</a> (essence of mowed lawns) and <a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">cinnamaldehyde</a> (essence of cinnamon). </p> <ul class="gallery mw-gallery-traditional skin-invert"> <li class="gallerycaption">Other α,β-unsaturated carbonyls</li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Crotonaldehyde.png" class="mw-file-description" title="E-Crotonaldehyde, an enal that exists as an isomer"><img alt="E-Crotonaldehyde, an enal that exists as an isomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Crotonaldehyde.png/120px-Crotonaldehyde.png" decoding="async" width="120" height="37" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Crotonaldehyde.png/180px-Crotonaldehyde.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Crotonaldehyde.png/240px-Crotonaldehyde.png 2x" data-file-width="6000" data-file-height="1838" /></a></span></div> <div class="gallerytext"><i>E</i>-<a href="/wiki/Crotonaldehyde" title="Crotonaldehyde">Crotonaldehyde</a>, an enal that exists as an isomer</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Cyclohexenone.png" class="mw-file-description" title="Cyclohexenone, common cyclic enone"><img alt="Cyclohexenone, common cyclic enone" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Cyclohexenone.png/55px-Cyclohexenone.png" decoding="async" width="55" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Cyclohexenone.png/82px-Cyclohexenone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/19/Cyclohexenone.png/110px-Cyclohexenone.png 2x" data-file-width="442" data-file-height="802" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cyclohexenone" title="Cyclohexenone">Cyclohexenone</a>, common cyclic enone</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Testosteron.svg" class="mw-file-description" title="testosterone, the male sex hormone"><img alt="testosterone, the male sex hormone" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/120px-Testosteron.svg.png" decoding="async" width="120" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/180px-Testosteron.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/240px-Testosteron.svg.png 2x" data-file-width="512" data-file-height="341" /></a></span></div> <div class="gallerytext"><a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, the male sex hormone</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Zimtaldehyd_-_cinnamaldehyde.svg" class="mw-file-description" title="Cinnamaldehyde, essence of cinnamon"><img alt="Cinnamaldehyde, essence of cinnamon" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Zimtaldehyd_-_cinnamaldehyde.svg/120px-Zimtaldehyd_-_cinnamaldehyde.svg.png" decoding="async" width="120" height="72" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Zimtaldehyd_-_cinnamaldehyde.svg/180px-Zimtaldehyd_-_cinnamaldehyde.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Zimtaldehyd_-_cinnamaldehyde.svg/240px-Zimtaldehyd_-_cinnamaldehyde.svg.png 2x" data-file-width="214" data-file-height="129" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">Cinnamaldehyde</a>, essence of cinnamon</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:P-Benzochinon.svg" class="mw-file-description" title="Paraquinone, a particularly electrophilic α,β-unsaturated carbonyl"><img alt="Paraquinone, a particularly electrophilic α,β-unsaturated carbonyl" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/P-Benzochinon.svg/39px-P-Benzochinon.svg.png" decoding="async" width="39" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/P-Benzochinon.svg/59px-P-Benzochinon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/P-Benzochinon.svg/79px-P-Benzochinon.svg.png 2x" data-file-width="70" data-file-height="176" /></a></span></div> <div class="gallerytext"><a href="/wiki/Paraquinone" class="mw-redirect" title="Paraquinone">Paraquinone</a>, a particularly electrophilic α,β-unsaturated carbonyl</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:(benzylideneacetone)iron-tricarbonyl-2D-skeletal.png" class="mw-file-description" title="Enone complex of iron tricarbonyl"><img alt="Enone complex of iron tricarbonyl" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/%28benzylideneacetone%29iron-tricarbonyl-2D-skeletal.png/120px-%28benzylideneacetone%29iron-tricarbonyl-2D-skeletal.png" decoding="async" width="120" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/%28benzylideneacetone%29iron-tricarbonyl-2D-skeletal.png/180px-%28benzylideneacetone%29iron-tricarbonyl-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fd/%28benzylideneacetone%29iron-tricarbonyl-2D-skeletal.png/240px-%28benzylideneacetone%29iron-tricarbonyl-2D-skeletal.png 2x" data-file-width="1100" data-file-height="906" /></a></span></div> <div class="gallerytext">Enone complex of iron tricarbonyl</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 130px;"><span typeof="mw:File"><a href="/wiki/File:Squaric_acid.svg" class="mw-file-description" title="Squaric acid"><img alt="Squaric acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Squaric_acid.svg/109px-Squaric_acid.svg.png" decoding="async" width="109" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Squaric_acid.svg/163px-Squaric_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Squaric_acid.svg/217px-Squaric_acid.svg.png 2x" data-file-width="179" data-file-height="165" /></a></span></div> <div class="gallerytext"><a href="/wiki/Squaric_acid" title="Squaric acid">Squaric acid</a></div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Reactions_of_α,β-unsaturated_carbonyls"><span id="Reactions_of_.CE.B1.2C.CE.B2-unsaturated_carbonyls"></span>Reactions of α,β-unsaturated carbonyls</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91,%CE%B2-Unsaturated_carbonyl_compound&action=edit&section=7" title="Edit section: Reactions of α,β-unsaturated carbonyls"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>α,β-Unsaturated carbonyls are <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a> at both the <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> carbon as well as the β-carbon. Depending on conditions, either site is attacked by <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a>. Additions to the alkene are called <a href="/wiki/Conjugate_addition" class="mw-redirect" title="Conjugate addition">conjugate additions</a>. One type of conjugate addition is the <a href="/wiki/Michael_addition" class="mw-redirect" title="Michael addition">Michael addition</a>, which is used commercially in the conversion of <a href="/wiki/Mesityl_oxide" title="Mesityl oxide">mesityl oxide</a> into <a href="/wiki/Isophorone" title="Isophorone">isophorone</a>. Owing to their extended conjugation, α,β-unsaturated carbonyls are prone to polymerization. In terms of industrial scale, polymerization dominates the use of α,β-unsaturated carbonyls. Again because of their electrophilic character, the alkene portion of α,β-unsaturated carbonyls is good dienophiles in <a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reactions</a>. They can be further activated by Lewis acids, which bind to the carbonyl oxygen. α,β-Unsaturated carbonyls are good ligands for low-valent metal complexes, examples being <a href="/wiki/(Benzylideneacetone)iron_tricarbonyl" title="(Benzylideneacetone)iron tricarbonyl">(bda)Fe(CO)<sub>3</sub></a> and <a href="/wiki/Tris(dibenzylideneacetone)dipalladium(0)" title="Tris(dibenzylideneacetone)dipalladium(0)">tris(dibenzylideneacetone)dipalladium(0)</a>. </p><p>α,β-Unsaturated carbonyls are readily hydrogenated. Hydrogenation can target the carbonyl or the alkene (<a href="/wiki/Conjugate_reduction" class="mw-redirect" title="Conjugate reduction">conjugate reduction</a>) selectively, or both functional groups. </p><p>Enones undergo the <a href="/wiki/Nazarov_cyclization_reaction" title="Nazarov cyclization reaction">Nazarov cyclization reaction</a> and in the <a href="/wiki/Rauhut%E2%80%93Currier_reaction" title="Rauhut–Currier reaction">Rauhut–Currier reaction</a> (dimerization). </p> <div class="mw-heading mw-heading2"><h2 id="α,β-Unsaturated_thioesters"><span id=".CE.B1.2C.CE.B2-Unsaturated_thioesters"></span>α,β-Unsaturated thioesters</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91,%CE%B2-Unsaturated_carbonyl_compound&action=edit&section=8" title="Edit section: α,β-Unsaturated thioesters"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>α,β-Unsaturated thioesters are intermediates in several enzymatic processes. Two prominent examples are <a href="/wiki/Coumaroyl-coenzyme_A" class="mw-redirect" title="Coumaroyl-coenzyme A">coumaroyl-coenzyme A</a> and <a href="/wiki/Crotonyl-coenzyme_A" class="mw-redirect" title="Crotonyl-coenzyme A">crotonyl-coenzyme A</a>. They arise by the action of <a href="/wiki/Acyl-CoA_dehydrogenase" title="Acyl-CoA dehydrogenase">acyl-CoA dehydrogenases</a>.<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> <a href="/wiki/Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">Flavin adenine dinucleotide</a> (FAD) is a required co-factor. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Beta-Oxidation1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Beta-Oxidation1.svg/500px-Beta-Oxidation1.svg.png" decoding="async" width="500" height="97" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Beta-Oxidation1.svg/750px-Beta-Oxidation1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Beta-Oxidation1.svg/1000px-Beta-Oxidation1.svg.png 2x" data-file-width="771" data-file-height="149" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%91,%CE%B2-Unsaturated_carbonyl_compound&action=edit&section=9" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Since α,β-unsaturated compounds are electrophiles and alkylating agents, many α,β-unsaturated carbonyl compounds are toxic. The endogenous scavenger compound <a href="/wiki/Glutathione" title="Glutathione">glutathione</a> naturally protects from toxic electrophiles in the body. Some drugs (amifostine, <a href="/wiki/N-acetylcysteine" class="mw-redirect" title="N-acetylcysteine"><i>N</i>-acetylcysteine</a>) containing thiol groups may protect from such harmful alkylation. </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=%CE%91,%CE%B2-Unsaturated_carbonyl_compound&action=edit&section=10" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/2-alkenal_reductase" title="2-alkenal reductase">2-alkenal reductase</a></li> <li><a href="/wiki/Dicarbonyls" class="mw-redirect" title="Dicarbonyls">Dicarbonyls</a></li> <li><a href="/wiki/Enol" title="Enol">Enol</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=%CE%91,%CE%B2-Unsaturated_carbonyl_compound&action=edit&section=11" 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 .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="CITEREFPataiRappoport1989" class="citation book cs1">Patai, Saul; Rappoport, Zvi, eds. (1989). <i>Enones</i>. Patai's Chemistry of Functional Groups. Vol. 1. <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%2F9780470772218">10.1002/9780470772218</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470772218" title="Special:BookSources/9780470772218"><bdi>9780470772218</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Enones&rft.series=Patai%27s+Chemistry+of+Functional+Groups&rft.date=1989&rft_id=info%3Adoi%2F10.1002%2F9780470772218&rft.isbn=9780470772218&rfr_id=info%3Asid%2Fen.wikipedia.org%3A%CE%91%2C%CE%B2-Unsaturated+carbonyl+compound" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPataiRappoport1989" class="citation book cs1">Patai, Saul; Rappoport, Zvi, eds. (1989). <i>Enones</i>. Patai's Chemistry of Functional Groups. Vol. 2. <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%2F9780470772225">10.1002/9780470772225</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470772225" title="Special:BookSources/9780470772225"><bdi>9780470772225</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Enones&rft.series=Patai%27s+Chemistry+of+Functional+Groups&rft.date=1989&rft_id=info%3Adoi%2F10.1002%2F9780470772225&rft.isbn=9780470772225&rfr_id=info%3Asid%2Fen.wikipedia.org%3A%CE%91%2C%CE%B2-Unsaturated+carbonyl+compound" class="Z3988"></span></span> </li> <li id="cite_note-March-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-March_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-March_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-March_3-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSmithMarch2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></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&rft.place=New+York&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.aulast=Smith&rft.aufirst=Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3A%CE%91%2C%CE%B2-Unsaturated+carbonyl+compound" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ullmann_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOharaSatoShimizuPrescher2003" class="citation encyclopaedia cs1">Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut (2003). 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(1 June 1995). <a rel="nofollow" class="external text" href="https://doi.org/10.1096%2Ffasebj.9.9.7601336">"Structure and mechanism of action of the Acyl-CoA dehydrogenases"</a>. <i><a href="/wiki/The_FASEB_Journal" title="The FASEB Journal">The FASEB Journal</a></i>. <b>9</b> (9): <span class="nowrap">718–</span>725. <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/10.1096%2Ffasebj.9.9.7601336">10.1096/fasebj.9.9.7601336</a></span>. <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/0892-6638">0892-6638</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/7601336">7601336</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:42549744">42549744</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+FASEB+Journal&rft.atitle=Structure+and+mechanism+of+action+of+the+Acyl-CoA+dehydrogenases&rft.volume=9&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E718-%3C%2Fspan%3E725&rft.date=1995-06-01&rft.issn=0892-6638&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A42549744%23id-name%3DS2CID&rft_id=info%3Apmid%2F7601336&rft_id=info%3Adoi%2F10.1096%2Ffasebj.9.9.7601336&rft.aulast=Thorpe&rft.aufirst=Colin&rft.au=Kim%2C+Jujng-Ja+P.&rft_id=https%3A%2F%2Fdoi.org%2F10.1096%252Ffasebj.9.9.7601336&rfr_id=info%3Asid%2Fen.wikipedia.org%3A%CE%91%2C%CE%B2-Unsaturated+carbonyl+compound" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" 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=Α,β-Unsaturated_carbonyl_compound&oldid=1273490218">https://en.wikipedia.org/w/index.php?title=Α,β-Unsaturated_carbonyl_compound&oldid=1273490218</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:Functional_groups" title="Category:Functional groups">Functional groups</a></li><li><a href="/wiki/Category:Conjugated_ketones" title="Category:Conjugated ketones">Conjugated ketones</a></li><li><a href="/wiki/Category:Alkene_derivatives" title="Category:Alkene derivatives">Alkene derivatives</a></li><li><a href="/wiki/Category:Enones" title="Category:Enones">Enones</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</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 2 February 2025, at 15:21<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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