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Sulfone - Wikipedia
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subsection</span> </button> <ul id="toc-Synthesis_and_reactions-sublist" class="vector-toc-list"> <li id="toc-By_oxidation_of_thioethers_and_sulfoxides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#By_oxidation_of_thioethers_and_sulfoxides"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>By oxidation of thioethers and sulfoxides</span> </div> </a> <ul id="toc-By_oxidation_of_thioethers_and_sulfoxides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_SO2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_SO2"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>From SO<sub>2</sub></span> </div> </a> <ul id="toc-From_SO2-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_sulfonyl_and_sulfuryl_halides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_sulfonyl_and_sulfuryl_halides"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>From sulfonyl and sulfuryl halides</span> </div> </a> <ul id="toc-From_sulfonyl_and_sulfuryl_halides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Reactions</span> </div> </a> <ul id="toc-Reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Applications</span> </div> </a> <button aria-controls="toc-Applications-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Applications subsection</span> </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Polymers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polymers"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Polymers</span> </div> </a> <ul id="toc-Polymers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Pharmacology</span> </div> </a> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> </ul> </li> </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">3</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" 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Available in 27 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-27" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">27 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D9%84%D9%81%D9%88%D9%86" title="سلفون – Arabic" lang="ar" hreflang="ar" data-title="سلفون" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Sulfona" title="Sulfona – Catalan" lang="ca" hreflang="ca" data-title="Sulfona" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Sulfony" title="Sulfony – Czech" lang="cs" hreflang="cs" data-title="Sulfony" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Sulfon" title="Sulfon – Danish" lang="da" hreflang="da" data-title="Sulfon" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Sulfone" title="Sulfone – German" lang="de" hreflang="de" data-title="Sulfone" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Sulfona" title="Sulfona – Spanish" lang="es" hreflang="es" data-title="Sulfona" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Sulfona" title="Sulfona – Basque" lang="eu" hreflang="eu" data-title="Sulfona" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%D9%88%D9%84%D9%81%D9%88%D9%86" title="سولفون – Persian" lang="fa" hreflang="fa" data-title="سولفون" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Sulfone" title="Sulfone – French" lang="fr" hreflang="fr" data-title="Sulfone" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Sulfona" title="Sulfona – Galician" lang="gl" hreflang="gl" data-title="Sulfona" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Solfoni" title="Solfoni – Italian" lang="it" hreflang="it" data-title="Solfoni" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Szulfon" title="Szulfon – Hungarian" lang="hu" hreflang="hu" data-title="Szulfon" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Sulfon" title="Sulfon – Dutch" lang="nl" hreflang="nl" data-title="Sulfon" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B9%E3%83%AB%E3%83%9B%E3%83%B3" title="スルホン – Japanese" lang="ja" hreflang="ja" data-title="スルホン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%B8%E0%A8%B2%E0%A8%AB%E0%A8%BC%E0%A9%8B%E0%A8%A8" title="ਸਲਫ਼ੋਨ – Punjabi" lang="pa" hreflang="pa" data-title="ਸਲਫ਼ੋਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Sulfony" title="Sulfony – Polish" lang="pl" hreflang="pl" data-title="Sulfony" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Sulfona" title="Sulfona – Portuguese" lang="pt" hreflang="pt" data-title="Sulfona" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Sulfon%C4%83" title="Sulfonă – Romanian" lang="ro" hreflang="ro" data-title="Sulfonă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A1%D1%83%D0%BB%D1%8C%D1%84%D0%BE%D0%BD%D1%8B" title="Сульфоны – Russian" lang="ru" hreflang="ru" data-title="Сульфоны" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Sulfone" title="Sulfone – Simple English" lang="en-simple" hreflang="en-simple" data-title="Sulfone" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Sulfon" title="Sulfon – Serbian" lang="sr" hreflang="sr" data-title="Sulfon" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Sulfon" title="Sulfon – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Sulfon" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Sulfonit" title="Sulfonit – Finnish" lang="fi" hreflang="fi" data-title="Sulfonit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Sulfon" title="Sulfon – Swedish" lang="sv" hreflang="sv" data-title="Sulfon" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%9A%E0%AE%B2%E0%AF%8D%E0%AE%AA%E0%AF%8B%E0%AE%A9%E0%AF%8D" title="சல்போன் – Tamil" lang="ta" hreflang="ta" data-title="சல்போன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A1%D1%83%D0%BB%D1%8C%D1%84%D0%BE%D0%BD%D0%B8" title="Сульфони – Ukrainian" lang="uk" hreflang="uk" 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</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">Organosulfur compound of the form >S(=O)2</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Sulfone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Sulfone.svg/150px-Sulfone.svg.png" decoding="async" width="150" height="126" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Sulfone.svg/225px-Sulfone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Sulfone.svg/300px-Sulfone.svg.png 2x" data-file-width="512" data-file-height="431" /></a><figcaption>The structure of a sulfone</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Dimethylsulfone-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Dimethylsulfone-3D-vdW.png/220px-Dimethylsulfone-3D-vdW.png" decoding="async" width="220" height="189" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Dimethylsulfone-3D-vdW.png/330px-Dimethylsulfone-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Dimethylsulfone-3D-vdW.png/440px-Dimethylsulfone-3D-vdW.png 2x" data-file-width="1100" data-file-height="947" /></a><figcaption><a href="/wiki/Methylsulfonylmethane" title="Methylsulfonylmethane">Dimethyl sulfone</a>, an example of a sulfone</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>sulfone</b> is a <a href="/wiki/Organosulfur_compound" class="mw-redirect" title="Organosulfur compound">organosulfur compound</a> containing a <a href="/wiki/Sulfonyl" class="mw-redirect" title="Sulfonyl">sulfonyl</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">R−S(=O)<sub class="template-chem2-sub">2</sub>−R’</span>) <a href="/wiki/Functional_group" title="Functional group">functional group</a> attached to two <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms. The central <a href="/wiki/Valence_(chemistry)" title="Valence (chemistry)">hexavalent</a> <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> atom is <a href="/wiki/Double-bond" class="mw-redirect" title="Double-bond">double-bonded</a> to each of two <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> atoms and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon <a href="/wiki/Substituent" title="Substituent">substituents</a>.<sup id="cite_ref-ISBN_9780534389512_1-0" class="reference"><a href="#cite_note-ISBN_9780534389512-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis_and_reactions">Synthesis and reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfone&action=edit&section=1" title="Edit section: Synthesis and reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="By_oxidation_of_thioethers_and_sulfoxides">By oxidation of thioethers and sulfoxides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfone&action=edit&section=2" title="Edit section: By oxidation of thioethers and sulfoxides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sulfones are typically prepared by <a href="/wiki/Organic_oxidation" class="mw-redirect" title="Organic oxidation">organic oxidation</a> of <a href="/wiki/Thioether" class="mw-redirect" title="Thioether">thioethers</a>, often referred to as <a href="/wiki/Sulfide" title="Sulfide">sulfides</a>. <a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxides</a> are intermediates in this route.<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> For example, <a href="/wiki/Dimethyl_sulfide" title="Dimethyl sulfide">dimethyl sulfide</a> oxidizes to <a href="/wiki/Dimethyl_sulfoxide" title="Dimethyl sulfoxide">dimethyl sulfoxide</a> and then to <a href="/wiki/Methylsulfonylmethane" title="Methylsulfonylmethane">dimethyl sulfone</a>.<sup id="cite_ref-ISBN_9780534389512_1-1" class="reference"><a href="#cite_note-ISBN_9780534389512-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="From_SO2">From SO<sub>2</sub></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfone&action=edit&section=3" title="Edit section: From SO2"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dd><figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Sulfolane_synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Sulfolane_synthesis.png/330px-Sulfolane_synthesis.png" decoding="async" width="330" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Sulfolane_synthesis.png/495px-Sulfolane_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Sulfolane_synthesis.png/660px-Sulfolane_synthesis.png 2x" data-file-width="1567" data-file-height="475" /></a><figcaption>Synthesis of sulfolane by <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> of <a href="/wiki/Sulfolene" title="Sulfolene">sulfolene</a>.</figcaption></figure></dd></dl> <p><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a> is a convenient and widely used source of the sulfonyl functional group. Specifically, Sulfur dioxide participates in cycloaddition reactions with dienes.<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> The industrially useful solvent <a href="/wiki/Sulfolane" title="Sulfolane">sulfolane</a> is prepared by addition of sulfur dioxide to <a href="/wiki/Butadiene" title="Butadiene">buta-1,3-diene</a> followed by hydrogenation of the resulting sulfolene.<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> </p> <div class="mw-heading mw-heading3"><h3 id="From_sulfonyl_and_sulfuryl_halides">From sulfonyl and sulfuryl halides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfone&action=edit&section=4" title="Edit section: From sulfonyl and sulfuryl halides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sulfones are prepared under conditions used for <a href="/wiki/Friedel%E2%80%93Crafts_reaction" title="Friedel–Crafts reaction">Friedel–Crafts reactions</a> using sources of <span class="chemf nowrap">RSO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> derived from <a href="/wiki/Sulfonyl_halides" class="mw-redirect" title="Sulfonyl halides">sulfonyl halides</a> and <a href="/wiki/Methanesulfonic_anhydride" title="Methanesulfonic anhydride">sulfonic acid anhydrides</a>. <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a> catalysts such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">AlCl<sub class="template-chem2-sub">3</sub></span> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">FeCl<sub class="template-chem2-sub">3</sub></span> are required.<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><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><p>Sulfones have been prepared by <a href="/wiki/Nucleophilic_displacement" class="mw-redirect" title="Nucleophilic displacement">nucleophilic displacement</a> of <a href="/wiki/Halide" title="Halide">halides</a> by <a href="/wiki/Sulfinate" class="mw-redirect" title="Sulfinate">sulfinates</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> <span class="mwe-math-element"><span class="mwe-math-mathml-display mwe-math-mathml-a11y" style="display: none;"><math display="block" xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {ArSO2Na + Ar'Cl -> Ar(Ar')SO2 + NaCl}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>ArSO</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>Na</mtext> <mo>+</mo> <msup> <mtext>Ar</mtext> <mo>′</mo> </msup> <mtext>Cl</mtext> <mo stretchy="false">⟶<!-- ⟶ --></mo> <mtext>Ar</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msup> <mtext>Ar</mtext> <mo>′</mo> </msup> <mo stretchy="false">)</mo> </mrow> <msubsup> <mtext>SO</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> <mtext>NaCl</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {ArSO2Na + Ar'Cl -> Ar(Ar')SO2 + NaCl}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/5417786f3ed60718a62edfc38cdd459157847cb0" class="mwe-math-fallback-image-display mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:43.345ex; height:3.176ex;" alt="{\displaystyle {\ce {ArSO2Na + Ar'Cl -> Ar(Ar')SO2 + NaCl}}}"></span> In general, relatively nonpolar ("<a href="/wiki/HSAB" class="mw-redirect" title="HSAB">soft</a>") alkylating agents react with sulfinic acids to give sulfones, whereas polarized ("hard") alkylating agents form esters.<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> <a href="/wiki/Allyl" class="mw-redirect" title="Allyl">Allyl</a>, <a href="/wiki/Propargyl" class="mw-redirect" title="Propargyl">propargyl</a>,<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Benzyl" class="mw-redirect" title="Benzyl">benzyl</a><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> sulfinates can thermally rearrange to the sulfone, but esters without an activated bond generally do not rearrange so.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Reactions">Reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfone&action=edit&section=5" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sulfone is a relatively inert functional group, typically less oxidizing and 4 <a href="/wiki/Bel_(unit)" class="mw-redirect" title="Bel (unit)">bel</a> more acidic than sulfoxides. In the <a href="/wiki/Ramberg%E2%80%93B%C3%A4cklund_reaction" title="Ramberg–Bäcklund reaction">Ramberg–Bäcklund reaction</a> and the <a href="/wiki/Julia_olefination" title="Julia olefination">Julia olefination</a>, sulfones are converted to <a href="/wiki/Alkene" title="Alkene">alkenes</a> by the elimination of <a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">sulfur dioxide</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> However, sulfones are unstable to bases, <a href="/wiki/Elimination_reaction" title="Elimination reaction">eliminating</a> to give an alkene.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Sulfones can also undergo <a href="/wiki/Desulfonylation_reactions" title="Desulfonylation reactions">desulfonylation</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfone&action=edit&section=6" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Sulfolane" title="Sulfolane">Sulfolane</a> is used to extract valuable aromatic compounds from petroleum.<sup id="cite_ref-Ullmann_4-1" class="reference"><a href="#cite_note-Ullmann-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Polymers">Polymers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfone&action=edit&section=7" title="Edit section: Polymers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some polymers containing sulfone groups are useful engineering plastics. They exhibit high strength and resistance to oxidation, corrosion, high temperatures, and creep under stress. For example, some are valuable as replacements for copper in domestic hot water plumbing.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Precursors to such polymers are the sulfones <a href="/wiki/Bisphenol_S" title="Bisphenol S">bisphenol S</a> and <a href="/wiki/4,4%27-Dichlorodiphenyl_sulfone" title="4,4'-Dichlorodiphenyl sulfone">4,4′-dichlorodiphenyl sulfone</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacology">Pharmacology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfone&action=edit&section=8" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Dapsone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Dapsone.svg/222px-Dapsone.svg.png" decoding="async" width="222" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Dapsone.svg/333px-Dapsone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Dapsone.svg/444px-Dapsone.svg.png 2x" data-file-width="512" data-file-height="219" /></a><figcaption><a href="/wiki/Dapsone" title="Dapsone">Dapsone</a>, an <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> used for the treatment of <a href="/wiki/Leprosy" title="Leprosy">leprosy</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Examples of sulfones in pharmacology include <a href="/wiki/Dapsone" title="Dapsone">dapsone</a>, a drug formerly used as an <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> to treat <a href="/wiki/Leprosy" title="Leprosy">leprosy</a>, <a href="/wiki/Dermatitis_herpetiformis" title="Dermatitis herpetiformis">dermatitis herpetiformis</a>, <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a>, or <a href="/wiki/Pneumocystis_pneumonia" title="Pneumocystis pneumonia">pneumocystis pneumonia</a> (PCP). Several of its derivatives, such as <a href="/wiki/Promin" title="Promin">promin</a>, have similarly been studied or actually been applied in medicine, but in general sulfones are of far less prominence in pharmacology than for example the <a href="/wiki/Sulfonamide_(medicine)" title="Sulfonamide (medicine)">sulfonamides</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </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=Sulfone&action=edit&section=9" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Sulfones" class="extiw" title="commons:Category:Sulfones">Sulfones</a></span>.</div></div> </div> <ul><li><a href="/wiki/Organosulfur_chemistry" title="Organosulfur chemistry">Organosulfur chemistry</a></li> <li><a href="/wiki/Sulfonanilide" title="Sulfonanilide">Sulfonanilide</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a> (–OH substituent)</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=Sulfone&action=edit&section=10" 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 reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-ISBN_9780534389512-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-ISBN_9780534389512_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ISBN_9780534389512_1-1"><sup><i><b>b</b></i></sup></a></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="CITEREFHornback2006" class="citation book cs1">Hornback, Joseph (2006). <i>Organic Chemistry</i>. 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"Sulfinic Acids and Derivatives". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. p. 682. <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%2F14356007.a25_461">10.1002/14356007.a25_461</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Sulfinic+Acids+and+Derivatives&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pages=682&rft.pub=Wiley-VCH&rft_id=info%3Adoi%2F10.1002%2F14356007.a25_461&rft.isbn=978-3527306732&rft.aulast=Schubart&rft.aufirst=R%26uuml%3Bdiger&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfone" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_encyclopedia" title="Template:Cite encyclopedia">cite encyclopedia</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text">S. Braverman and T. Pechenick, <i>Tetrahedron Lett.</i>, 43, 499 (2002). <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2801%2902174-8">10.1016/S0040-4039(01)02174-8</a></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKenyonPhillips1930" class="citation journal cs1">Kenyon, Joseph; Phillips, Henry (3 June 1930). "The optical instability of tercovalent carbonium kations". <i>Journal of the Chemical Society</i>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FJR9300001676">10.1039/JR9300001676</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Chemical+Society&rft.atitle=The+optical+instability+of+tercovalent+carbonium+kations&rft.date=1930-06-03&rft_id=info%3Adoi%2F10.1039%2FJR9300001676&rft.aulast=Kenyon&rft.aufirst=Joseph&rft.au=Phillips%2C+Henry&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfone" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCopeMorrisonField1950" class="citation journal cs1">Cope, Arthur C.; Morrison, Dwight E.; Field, Lamar (Jan 1950) [21 June 1949]. "Thermal rearrangement of allyl-type sulfoxides, sulfones and sulfinates". <i>Journal of the ACS</i>. <b>72</b>: 60. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01157a018">10.1021/ja01157a018</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+ACS&rft.atitle=Thermal+rearrangement+of+allyl-type+sulfoxides%2C+sulfones+and+sulfinates&rft.volume=72&rft.pages=60&rft.date=1950-01&rft_id=info%3Adoi%2F10.1021%2Fja01157a018&rft.aulast=Cope&rft.aufirst=Arthur+C.&rft.au=Morrison%2C+Dwight+E.&rft.au=Field%2C+Lamar&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfone" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCareySundberg2007" class="citation book cs1">Carey, Francis A.; Sundberg, Richard J. (2007). <i>Advanced Organic Chemistry</i>. Berlin: Springer. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-387-68354-6" title="Special:BookSources/978-0-387-68354-6"><bdi>978-0-387-68354-6</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&rft.place=Berlin&rft.pub=Springer&rft.date=2007&rft.isbn=978-0-387-68354-6&rft.aulast=Carey&rft.aufirst=Francis+A.&rft.au=Sundberg%2C+Richard+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfone" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text">Smith (2020), <i>March's Organic Chemistry</i>, rxn. 17-10.</span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFink2008" class="citation book cs1">Fink, Johannes (2008). <i>High Performance Polymers</i>. Norwich: William Andrew. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8155-1580-7" title="Special:BookSources/978-0-8155-1580-7"><bdi>978-0-8155-1580-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=High+Performance+Polymers&rft.place=Norwich&rft.pub=William+Andrew&rft.date=2008&rft.isbn=978-0-8155-1580-7&rft.aulast=Fink&rft.aufirst=Johannes&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfone" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFThomas_L._Lemke2008" class="citation book cs1">Thomas L. Lemke (2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=R0W1ErpsQpkC&pg=PA1142"><i>Foye's Principles of Medicinal Chemistry</i></a>. Lippincott Williams & Wilkins. p. 1142. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780781768795" title="Special:BookSources/9780781768795"><bdi>9780781768795</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160304193954/https://books.google.ca/books?id=R0W1ErpsQpkC&pg=PA1142">Archived</a> from the original on 2016-03-04.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Foye%27s+Principles+of+Medicinal+Chemistry&rft.pages=1142&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2008&rft.isbn=9780781768795&rft.au=Thomas+L.+Lemke&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DR0W1ErpsQpkC%26pg%3DPA1142&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfone" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCraigStitzel2004" class="citation book cs1">Craig, Charles R.; Stitzel, Robert E. (2004). <i>Modern Pharmacology with Clinical Applications</i>. Hagerstwon: Lippincott Williams & Wilkins. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-3762-3" title="Special:BookSources/978-0-7817-3762-3"><bdi>978-0-7817-3762-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Modern+Pharmacology+with+Clinical+Applications&rft.place=Hagerstwon&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2004&rft.isbn=978-0-7817-3762-3&rft.aulast=Craig&rft.aufirst=Charles+R.&rft.au=Stitzel%2C+Robert+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfone" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDrillDi_Palma1971" class="citation book cs1">Drill, Victor Alexander; Di Palma, Joseph R. (1971). <i>Drill's Pharmacology in Medicine</i>. New York: McGraw-Hill. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-07-017006-3" title="Special:BookSources/978-0-07-017006-3"><bdi>978-0-07-017006-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drill%27s+Pharmacology+in+Medicine&rft.place=New+York&rft.pub=McGraw-Hill&rft.date=1971&rft.isbn=978-0-07-017006-3&rft.aulast=Drill&rft.aufirst=Victor+Alexander&rft.au=Di+Palma%2C+Joseph+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfone" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output 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style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a class="mw-selflink selflink">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <!-- NewPP limit report Parsed by mw‐api‐int.codfw.main‐849f99967d‐62ftq Cached time: 20241123045142 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.427 seconds Real time usage: 0.582 seconds Preprocessor visited node count: 1768/1000000 Post‐expand include size: 69540/2097152 bytes Template argument size: 1527/2097152 bytes Highest expansion depth: 16/100 Expensive parser function count: 1/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 70918/5000000 bytes Lua time usage: 0.270/10.000 seconds Lua memory usage: 6496634/52428800 bytes Number of Wikibase entities loaded: 1/400 --> <!-- 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