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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Hypervalenz</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><p>Als <b>Hypervalenz</b> [griech. hyper: über, zu viel, siehe <a href="Liste_griechischer_Pr%C3%A4fixe" title="Liste griechischer Präfixe">Liste griechischer Präfixe</a>] wird die positive Abweichung zur <a href="Valenzstrukturtheorie" class="mw-redirect" title="Valenzstrukturtheorie">Valenzstrukturtheorie</a> bezeichnet, nach der die <a href="Schalenmodell_(Atomphysik)" title="Schalenmodell (Atomphysik)">äußere Schale</a> eines Atoms mehr als die nach der <a href="Edelgaskonfiguration" title="Edelgaskonfiguration">Edelgaskonfiguration</a> von s- und p-Orbitalen möglichen acht <a href="Elektron" title="Elektron">Elektronen</a> aufnehmen kann (<a href="Oktettregel" title="Oktettregel">Oktettregel</a>). Sie tritt bei Verbindungen von schweren <a href="Hauptgruppe" title="Hauptgruppe">Hauptgruppenelementen</a> der 3. bis 8. Hauptgruppe mit starken <a href="Elektronenakzeptor" title="Elektronenakzeptor">Elektronenakzeptoren</a> wie <a href="Sauerstoff" title="Sauerstoff">Sauerstoff</a> oder <a href="Fluor" title="Fluor">Fluor</a> auf.<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> So zum Beispiel in Selenhalogeniden wie <a href="Selenhexafluorid" title="Selenhexafluorid">Selenhexafluorid</a> (SeF<sub>6</sub>) oder Iodfluoriden (z. B. IF<sub>5</sub>, IF<sub>7</sub>), generell in vielen <a href="Edelgasverbindungen" title="Edelgasverbindungen">Edelgas-</a> und <a href="Interhalogenverbindungen" title="Interhalogenverbindungen">Interhalogenverbindungen</a>. Es wurde eine Beteiligung der <a href="D-Orbital" class="mw-redirect" title="D-Orbital">d-Orbitale</a> des Zentralatoms angenommen, was allerdings inzwischen als nicht korrekt gilt. Heutzutage wird die Beschreibung durch eine elektronenreiche <a href="Mehrzentrenbindung" title="Mehrzentrenbindung">Mehrzentrenbindung</a> realisiert.
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<div class="mw-heading mw-heading2"><h2 id="Beispiele">Beispiele</h2></div>
<div class="mw-heading mw-heading3"><h3 id="Hypervalente_Iodverbindungen">Hypervalente Iodverbindungen</h3></div>
<p>In der organischen Synthesechemie werden hypervalente Iodverbindungen als milde <a href="Oxidationsmittel" title="Oxidationsmittel">Oxidationsmittel</a> vielfach eingesetzt.<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> Zu diesen „modernen“ Oxidationsmitteln zählen u. a:
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<td><a href="Iodosylbenzol" class="mw-redirect" title="Iodosylbenzol">Iodosylbenzol</a><sup id="cite_ref-Zhdankin2002_3-0" class="reference"><a href="#cite_note-Zhdankin2002-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wirth2005_4-0" class="reference"><a href="#cite_note-Wirth2005-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
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<td><a href="Diacetoxyiodbenzol" title="Diacetoxyiodbenzol">Diacetoxyiodbenzol</a> (DIB)<sup id="cite_ref-Zhdankin2002_3-1" class="reference"><a href="#cite_note-Zhdankin2002-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wirth2005_4-1" class="reference"><a href="#cite_note-Wirth2005-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wirth2006_5-0" class="reference"><a href="#cite_note-Wirth2006-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
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<td><a href="Iodbenzoldichlorid" title="Iodbenzoldichlorid">Iodbenzoldichlorid</a><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>
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<td><a href="Dess-Martin-Periodinan" title="Dess-Martin-Periodinan">Dess-Martin-Periodinan</a> (DMP)<sup id="cite_ref-Zhdankin2002_3-2" class="reference"><a href="#cite_note-Zhdankin2002-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wirth2005_4-2" class="reference"><a href="#cite_note-Wirth2005-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
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<td><a href="2-Iodoxybenzoes%C3%A4ure" title="2-Iodoxybenzoesäure">2-Iodoxybenzoesäure</a> (IBX)<sup id="cite_ref-Zhdankin2002_3-3" class="reference"><a href="#cite_note-Zhdankin2002-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wirth2005_4-3" class="reference"><a href="#cite_note-Wirth2005-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wirth2006_5-1" class="reference"><a href="#cite_note-Wirth2006-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
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<td><a href="2-Iodosylbenzoes%C3%A4ure" title="2-Iodosylbenzoesäure">2-Iodosylbenzoesäure</a> (IBA)<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>
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<p><a href="Dess-Martin-Periodinan" title="Dess-Martin-Periodinan">Dess-Martin-Periodinan</a> wird besonders in der so genannten <a href="Dess-Martin-Oxidation" class="mw-redirect" title="Dess-Martin-Oxidation">Dess-Martin-Oxidation</a> eingesetzt. Weiterhin gibt es Reagenzien mit hypervalentem Iod, die zur elektrophilen Einführung von Iod (Angriff von I<sup>+</sup> auf <a href="Nucleophil" class="mw-redirect" title="Nucleophil">Nucleophile</a>, z. B. C=C-<a href="Doppelbindung" title="Doppelbindung">Doppelbindungen</a>) dienen:
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<td>Di-<i>sym</i>-collidin-iodoniumperchlorat<sup id="cite_ref-Danishefsky1990_9-0" class="reference"><a href="#cite_note-Danishefsky1990-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>
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<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a></span> <span class="reference-text">Eintrag zu <i>hypervalency.</i> In: <a href="International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a> (Hrsg.): <i><a href="Compendium_of_Chemical_Terminology" title="Compendium of Chemical Terminology">Compendium of Chemical Terminology</a>.</i> The “Gold Book”. <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/10.1351/goldbook.HT07054">10.1351/goldbook.HT07054</a></span> – Version: 2.3.2.</span>
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<li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">Akira Yoshimura, Viktor V. Zhdankin: <cite style="font-style:italic">Advances in Synthetic Applications of Hypervalent Iodine Compounds</cite>. In: <cite style="font-style:italic">Chemical Reviews</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>116</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>5</span>, 9. März 2016, <a href="Internationale_Standardnummer_f%C3%BCr_fortlaufende_Sammelwerke" title="Internationale Standardnummer für fortlaufende Sammelwerke">ISSN</a> <span style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://zdb-katalog.de/list.xhtml?t=iss%3D%220009-2665%22&key=cql">0009-2665</a></span>, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>3328–3435</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/acs.chemrev.5b00547">10.1021/acs.chemrev.5b00547</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:Hypervalenz&rft.atitle=Advances+in+Synthetic+Applications+of+Hypervalent+Iodine+Compounds&rft.au=Akira+Yoshimura%2C+Viktor+V.+Zhdankin&rft.date=2016-03-09&rft.doi=10.1021%2Facs.chemrev.5b00547&rft.genre=journal&rft.issn=0009-2665&rft.issue=5&rft.jtitle=Chemical+Reviews&rft.pages=3328-3435&rft.volume=116" style="display:none"> </span></span>
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<li id="cite_note-Zhdankin2002-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Zhdankin2002_3-0">a</a></sup> <sup><a href="#cite_ref-Zhdankin2002_3-1">b</a></sup> <sup><a href="#cite_ref-Zhdankin2002_3-2">c</a></sup> <sup><a href="#cite_ref-Zhdankin2002_3-3">d</a></sup></span> <span class="reference-text">V. V. Zhdankin, P. J. Stang: In: <i><a href="Chemical_Reviews" title="Chemical Reviews">Chemical Reviews</a>.</i> 102, 2002, S. 2523–2584.</span>
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<li id="cite_note-Wirth2005-4"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Wirth2005_4-0">a</a></sup> <sup><a href="#cite_ref-Wirth2005_4-1">b</a></sup> <sup><a href="#cite_ref-Wirth2005_4-2">c</a></sup> <sup><a href="#cite_ref-Wirth2005_4-3">d</a></sup></span> <span class="reference-text">T. Wirth: In: <i><a href="Angew._Chem." class="mw-redirect" title="Angew. Chem.">Angew. Chem.</a></i> 117, 2005, S. 3722–3731.</span>
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<li id="cite_note-Wirth2006-5"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Wirth2006_5-0">a</a></sup> <sup><a href="#cite_ref-Wirth2006_5-1">b</a></sup></span> <span class="reference-text">R. D. Richardson, T. Wirth: In: <i><a href="Angew._Chem." class="mw-redirect" title="Angew. Chem.">Angew. Chem.</a></i> 118, 2006, S. 4510–4512.</span>
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<li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">E. M. Archer, T. G. van Schalkwyk: <cite style="font-style:italic">The crystal structure of benzene iododichloride</cite>. In: <cite style="font-style:italic">Acta Crystallographica</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>6</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, 1. Januar 1953, <a href="Internationale_Standardnummer_f%C3%BCr_fortlaufende_Sammelwerke" title="Internationale Standardnummer für fortlaufende Sammelwerke">ISSN</a> <span style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://zdb-katalog.de/list.xhtml?t=iss%3D%220365-110X%22&key=cql">0365-110X</a></span>, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>88–92</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/10.1107/S0365110X53000193">10.1107/S0365110X53000193</a></span> (<a rel="nofollow" class="external text" href="https://journals.iucr.org/paper?S0365110X53000193">iucr.org</a> [abgerufen am 11. Juni 2025]).<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:Hypervalenz&rft.atitle=The+crystal+structure+of+benzene+iododichloride&rft.au=E.+M.+Archer%2C+T.+G.+van+Schalkwyk&rft.date=1953-01-01&rft.doi=10.1107%2FS0365110X53000193&rft.genre=journal&rft.issn=0365-110X&rft.issue=1&rft.jtitle=Acta+Crystallographica&rft.pages=88-92&rft.volume=6" style="display:none"> </span></span>
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<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">J. V. Carey, P. A. Chaloner, P. B. Hitchcock, T. Neugebauer, K. R. Seddon: <cite style="font-style:italic">ChemInform Abstract: Synthesis and Decomposition of Dichloroiodoarenes. An Improved Low Temperature X-Ray Structure of Dichloroiodobenzene and the Structure of 1-Chloro-2,3,5,6-tetrakis(chloromethyl)-4-methylbenzene.</cite> In: <cite style="font-style:italic">ChemInform</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>27</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>52</span>, 1996, <a href="Internationale_Standardnummer_f%C3%BCr_fortlaufende_Sammelwerke" title="Internationale Standardnummer für fortlaufende Sammelwerke">ISSN</a> <span style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://zdb-katalog.de/list.xhtml?t=iss%3D%221522-2667%22&key=cql">1522-2667</a></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/chin.199652032">10.1002/chin.199652032</a></span> (<a rel="nofollow" class="external text" href="https://onlinelibrary.wiley.com/doi/abs/10.1002/chin.199652032">wiley.com</a> [abgerufen am 11. Juni 2025]).<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:Hypervalenz&rft.atitle=ChemInform+Abstract%3A+Synthesis+and+Decomposition+of+Dichloroiodoarenes.+An+Improved+Low+Temperature+X-Ray+Structure+of+Dichloroiodobenzene+and+the+Structure+of+1-Chloro-2%2C3%2C5%2C6-tetrakis%28chloromethyl%29-4-methylbenzene.&rft.au=J.+V.+Carey%2C+P.+A.+Chaloner%2C+P.+B.+Hitchcock%2C+...&rft.date=1996&rft.doi=10.1002%2Fchin.199652032&rft.genre=journal&rft.issn=1522-2667&rft.issue=52&rft.jtitle=ChemInform&rft.volume=27" style="display:none"> </span></span>
</li>
<li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">Supanimit Chiampanichayakul, Manat Pohmakotr, Vichai Reutrakul, Thaworn Jaipetch, Chutima Kuhakarn: <cite style="font-style:italic">Oxidative Conversion of Amines into Their Corresponding Nitriles Using o -Iodoxybenzoic Acid (IBX)/Iodine: Selective Oxidation of Aminoalcohols to Hydroxynitriles</cite>. In: <cite style="font-style:italic">Synthesis</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>2008</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>13</span>, 11. Juni 2008, <a href="Internationale_Standardnummer_f%C3%BCr_fortlaufende_Sammelwerke" title="Internationale Standardnummer für fortlaufende Sammelwerke">ISSN</a> <span style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://zdb-katalog.de/list.xhtml?t=iss%3D%220039-7881%22&key=cql">0039-7881</a></span>, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>2045–2048</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/10.1055/s-2008-1067123">10.1055/s-2008-1067123</a></span> (<a rel="nofollow" class="external text" href="http://www.thieme-connect.de/DOI/DOI?10.1055/s-2008-1067123">thieme-connect.de</a> [abgerufen am 3. September 2025]).<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:Hypervalenz&rft.atitle=Oxidative+Conversion+of+Amines+into+Their+Corresponding+Nitriles+Using+o+-Iodoxybenzoic+Acid+%28IBX%29%2FIodine%3A+Selective+Oxidation+of+Aminoalcohols+to+Hydroxynitriles&rft.au=Supanimit+Chiampanichayakul%2C+Manat+Pohmakotr%2C+Vichai+Reutrakul%2C+...&rft.date=2008-06-11&rft.doi=10.1055%2Fs-2008-1067123&rft.genre=journal&rft.issn=0039-7881&rft.issue=13&rft.jtitle=Synthesis&rft.pages=2045-2048&rft.volume=2008" style="display:none"> </span></span>
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<li id="cite_note-Danishefsky1990-9"><span class="mw-cite-backlink"><a href="#cite_ref-Danishefsky1990_9-0">↑</a></span> <span class="reference-text">D. A. Griffith, <a href="Samuel_Danishefsky" title="Samuel Danishefsky">S. J. Danishefsky</a>: In: <i><a href="J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a></i> 112, 1990, S. 5811–5819.</span>
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