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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Dioxirane</span></h1>
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<th>Dioxirane
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<td><span typeof="mw:File"></span><br>(allgemeine Formel)
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<p><b>Dioxirane</b> sind <a href="Heterocyclen" title="Heterocyclen">heterocyclische</a> organisch-chemische Stoffe, die einen Dreiring bestehend aus zwei Sauerstoffatomen und einem Kohlenstoffatom enthalten. Die Oxazirane zählen zu der größeren Stoffgruppe der Dreiringverbindungen mit zwei <a href="Heteroatome" class="mw-redirect" title="Heteroatome">Heteroatomen</a> im Ring.<sup id="cite_ref-Joule_1-0" class="reference"><a href="#cite_note-Joule-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Man kann die Dioxirane auch als cyclische Peroxide betrachten.<sup id="cite_ref-Murray_2-0" class="reference"><a href="#cite_note-Murray-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Folglich sind viele Dioxirane nur in Lösung stabil und sehr reaktionsfreudig. Oft werden die Dioxirane nur <i>in situ</i> hergestellt und dienen in der <a href="Organische_Chemie" title="Organische Chemie">Organischen Chemie</a> als <a href="Oxidationsmittel" title="Oxidationsmittel">Oxidationsmittel</a>.<sup id="cite_ref-Kirschfeld_3-0" class="reference"><a href="#cite_note-Kirschfeld-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
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<div class="mw-heading mw-heading2"><h2 id="Herstellung">Herstellung</h2></div>
<p>Dioxirane werden meist aus <a href="Ketone" title="Ketone">Ketonen</a> und <a href="Pers%C3%A4ure" class="mw-redirect" title="Persäure">Persäuren</a> (z. B. einem Salz der <a href="Peroxomonoschwefels%C3%A4ure" title="Peroxomonoschwefelsäure">Peroxomonoschwefelsäure</a>) synthetisiert.<sup id="cite_ref-Murray_2-1" class="reference"><a href="#cite_note-Murray-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Dimethyldioxiran kann durch Reaktion von <a href="Aceton" title="Aceton">Aceton</a> mit einer neutral gepufferten Lösung von <a href="Kaliumperoxomonosulfat" title="Kaliumperoxomonosulfat">Kaliumperoxomonosulfat</a> (Handelsnamen u. a. Oxone und Caroat) gewonnen werden:<sup id="cite_ref-eros_4-0" class="reference"><a href="#cite_note-eros-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
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<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>Präparative Bedeutung als Oxidationsmittel besitzen besonders <a href="Dimethyldioxiran" title="Dimethyldioxiran">Dimethyldioxiran</a> und Methyl(trifluormethyl)dioxiran.<sup id="cite_ref-Kirschfeld_3-1" class="reference"><a href="#cite_note-Kirschfeld-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
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<div class="mw-heading mw-heading2"><h2 id="Weblinks">Weblinks</h2></div>
<div class="sisterproject" style="margin:0.1em 0 0 0;"><div class="noresize noviewer" style="display:inline-block; line-height:10px; min-width:1.6em; text-align:center;" aria-hidden="true" role="presentation"><span class="mw-default-size" typeof="mw:File"><span title="Commons"></span></span></div><b><span class=""><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Dioxiranes?uselang=de"><span lang="en">Commons</span>: Dioxiranes</a></span></b> – Sammlung von Bildern, Videos und Audiodateien</div>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Joule-1"><span class="mw-cite-backlink"><a href="#cite_ref-Joule_1-0">↑</a></span> <span class="reference-text"><a href="John_A._Joule" title="John A. Joule">John A. Joule</a>, Keith Mills: <i>Heterocyclic Chemistry at a Glance</i>. 2. Auflage, Wiley & Sons, ISBN 978-0-470-97121-5, S. 596–597.</span>
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<li id="cite_note-Murray-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Murray_2-0">a</a></sup> <sup><a href="#cite_ref-Murray_2-1">b</a></sup></span> <span class="reference-text">Robert W. Murray: <cite style="font-style:italic">Chemistry of dioxiranes. 12. Dioxiranes</cite>. In: <cite style="font-style:italic">Chemical Reviews</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>89</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>5</span>, 1. Juli 1989, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>1187–1201</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1021/cr00095a013">10.1021/cr00095a013</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Dioxirane&rft.atitle=Chemistry+of+dioxiranes.+12.+Dioxiranes&rft.au=Robert+W.+Murray&rft.date=1989-07-01&rft.doi=10.1021%2Fcr00095a013&rft.genre=journal&rft.issue=5&rft.jtitle=Chemical+Reviews&rft.pages=1187-1201&rft.volume=89" style="display:none"> </span></span>
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<li id="cite_note-Kirschfeld-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Kirschfeld_3-0">a</a></sup> <sup><a href="#cite_ref-Kirschfeld_3-1">b</a></sup></span> <span class="reference-text">Andreas Kirschfeld, Sengodagounder Muthusamy, Wolfram Sander: <cite style="font-style:italic">Dimesityldioxiran — ein in Substanz stabiles Dioxiran</cite>. In: <cite style="font-style:italic">Angewandte Chemie</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>106</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>21</span>, 1994, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>2261–2263</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1002/ange.19941062108">10.1002/ange.19941062108</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Dioxirane&rft.atitle=Dimesityldioxiran+%E2%80%94+ein+in+Substanz+stabiles+Dioxiran&rft.au=Andreas+Kirschfeld%2C+Sengodagounder+Muthusamy%2C+Wolfram+Sander&rft.date=1994&rft.doi=10.1002%2Fange.19941062108&rft.genre=journal&rft.issue=21&rft.jtitle=Angewandte+Chemie&rft.pages=2261-2263&rft.volume=106" style="display:none"> </span></span>
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<li id="cite_note-eros-4"><span class="mw-cite-backlink"><a href="#cite_ref-eros_4-0">↑</a></span> <span class="reference-text">Jack K. Crandall, Ruggero Curci, Lucia D’Accolti, Caterina Fusco: <cite style="font-style:italic">Dimethyldioxirane</cite>. In: <cite style="font-style:italic">Encyclopedia of Reagents for Organic Synthesis</cite>. American Cancer Society, 2005, ISBN 978-0-470-84289-8, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1002/047084289X.rd329.pub2">10.1002/047084289X.rd329.pub2</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:Dioxirane&rft.atitle=Dimethyldioxirane&rft.au=Jack+K.+Crandall%2C+Ruggero+Curci%2C+Lucia+D%E2%80%99Accolti%2C+...&rft.btitle=Encyclopedia+of+Reagents+for+Organic+Synthesis&rft.date=2005&rft.doi=10.1002%2F047084289X.rd329.pub2&rft.genre=book&rft.isbn=9780470842898&rft.pub=American+Cancer+Society" style="display:none"> </span></span>
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