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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">1,2-Dibromcyclohexan</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"><table class="wikitable infobox float-right" id="Vorlage_Infobox_Chemikalie" style="font-size:90%; margin-top:0; width:350px;" summary="Infobox Chemikalie">
<tbody><tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
</th></tr>
<tr>
<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"></span>
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<tr>
<td colspan="2" style="text-align:center; font-size:80%;"><i>cis</i>- und <i>trans</i>-Dibromcyclohexan
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>1,2-Dibromcyclohexan
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>6</sub>H<sub>10</sub>Br<sub>2</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>farblose bis gelbliche Flüssigkeit<sup id="cite_ref-TCI_1-0" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
</th></tr>
<tr>
<td colspan="2" style="padding:0;">
<table class="mw-collapsible mw-collapsed wikitable" data-expandtext="+" data-collapsetext="−" style="border-top:none; margin:-1px; width:calc(100% + 2px);">
<tbody><tr>
<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td>
<ul><li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=5401-62-7">5401-62-7</a><span class="editoronly" style="display:none;"></span></li>
<li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=7429-37-0">7429-37-0</a><span class="editoronly" style="display:none;"></span> (<i>trans</i>-Form)</li>
<li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=5183-77-7">5183-77-7</a><span class="editoronly" style="display:none;"></span> ((±)-<i>trans</i>-Form)</li>
<li><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">34969-65-8</span><span class="editoronly" style="display:none;"></span> (<i>trans</i>-Form)</li>
<li><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">19246-38-9</span><span class="editoronly" style="display:none;"></span> (<i>cis</i>-Form)</li></ul>
</td>
<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
</td></tr>
<tr>
<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a>
</td>
<td colspan="2">226-449-4
</td></tr>
<tr>
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.024.045">100.024.045</a>
</td></tr>
<tr>
<td><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/95314">95314</a>
</td></tr>
<tr>
<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.86011.html">86011</a>
</td></tr>
<tr>
<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q82862715" class="extiw external" title="d:Q82862715">Q82862715</a>
</td></tr></tbody></table>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
<tr>
<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>241,95 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td>
<p>flüssig<sup id="cite_ref-TCI_1-1" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Dichte" title="Dichte">Dichte</a>
</td>
<td>
<p>1,79 g/mL (<i>trans</i>-Form)<sup id="cite_ref-TCI_1-2" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Siedepunkt" title="Siedepunkt">Siedepunkt</a>
</td>
<td>
<ul><li>102 °C (14 <a href="MmHg" class="mw-redirect" title="MmHg">mmHg</a>) (<i>trans</i>-Form)<sup id="cite_ref-TCI_1-3" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li>
<li>104 °C (9 mmHg) (<i>cis</i>-Form)<sup id="cite_ref-S._Coffey_2-0" class="reference"><a href="#cite_note-S._Coffey-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<p>löslich in Ethanol, Diethylether, Aceton und Benzol<sup id="cite_ref-Richard_Montgomery_Stephenson_3-0" class="reference"><a href="#cite_note-Richard_Montgomery_Stephenson-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Brechungsindex" title="Brechungsindex">Brechungsindex</a>
</td>
<td>
<ul><li>1,5506 (20 °C) (<i>trans</i>-Form)<sup id="cite_ref-S._Coffey_2-1" class="reference"><a href="#cite_note-S._Coffey-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li>
<li>1,5523 (25 °C)<sup id="cite_ref-S._Coffey_2-2" class="reference"><a href="#cite_note-S._Coffey-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
</th></tr>
<tr>
<td colspan="2">
<table cellspacing="0" cellpadding="2" style="width:100%;">
<tbody><tr>
<td colspan="2" style="text-align:center"><b><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-Gefahrstoffkennzeichnung</a></b><sup id="cite_ref-TCI_1-4" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
<p><i>trans</i>-Form
</p>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
<tbody><tr>
<td><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table>
<p>
</p>
</td></tr>
<tr>
<td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a>
</td>
<td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><i>keine H-Sätze</i>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i><sup id="cite_ref-TCI_1-5" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td></tr>
</tbody></table>
</td></tr>
<tr>
<td colspan="2" style="background:#FFDEAD; color:#202122; font-size:80%; text-align:center; line-height:150%; padding:.25em;">Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0 °C, 1000 hPa). Brechungsindex: <a href="Natrium-D-Linie" title="Natrium-D-Linie">Na-D-Linie</a>, 20 °C
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>1,2-Dibromcyclohexan</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Gruppe der <a href="Cyclohexan" title="Cyclohexan">Cyclohexanderivate</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Gewinnung_und_Darstellung">Gewinnung und Darstellung</h2></div>
<p>1,2-Dibromcyclohexan kann durch Reaktion von <a href="Cyclohexen" title="Cyclohexen">Cyclohexen</a> mit <a href="Brom" title="Brom">Brom</a> gewonnen werden, wobei die trans-Form entsteht.<sup id="cite_ref-Janice_Smith_4-0" class="reference"><a href="#cite_note-Janice_Smith-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-S._Coffey_2-3" class="reference"><a href="#cite_note-S._Coffey-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
<dl><dd></dd></dl>
<div style="clear:left;"></div>
<p>Die Addition von <a href="Bromwasserstoff" title="Bromwasserstoff">Bromwasserstoff</a> an <a href="1-Bromcyclohexen" title="1-Bromcyclohexen">1-Bromcyclohexen</a> ist insofern regioselektiv, als sie nur cis-1,2-Dibromcyclohexan ergibt.<sup id="cite_ref-Michael_B._Smith_5-0" class="reference"><a href="#cite_note-Michael_B._Smith-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>(±)-<i>trans</i>-1,2-Dibromcyclohexan ist eine farblose bis gelbliche, klare Flüssigkeit.<sup id="cite_ref-TCI_1-6" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Es gibt drei <a href="Stereoisomere" class="mw-redirect" title="Stereoisomere">Stereoisomere</a> von 1,2-Dibromcyclohexan, wobei die cis-Verbindung in zwei untereinander konvertierbaren <a href="Sesselkonformation" class="mw-redirect" title="Sesselkonformation">Sesselkonformationen</a> vorliegt. Sie liegt als <a href="Racemat" title="Racemat">racemisches</a> Gemisch vor, und es ist unmöglich, seine optisch aktive Probe zu erhalten. trans-1,2-Dibromcyclohexan hat keine Symmetrieebene und liegt als <a href="Enantiomere" class="mw-redirect" title="Enantiomere">Enantiomerenpaar</a> vor.<sup id="cite_ref-P.S._Kalsi_6-0" class="reference"><a href="#cite_note-P.S._Kalsi-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> Der Anteil der Konformere von trans-Dibromcyclohexan hängt vom Aggregatszustand und dem <a href="L%C3%B6sungsmittel" title="Lösungsmittel">Lösungsmittel</a> ab.<sup id="cite_ref-Metin_Balcı_8-0" class="reference"><a href="#cite_note-Metin_Balcı-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>
</p><p><i>cis</i>-1,2-Dibromcyclohexan kann durch Reaktion mit <a href="Kaliumiodid" title="Kaliumiodid">Kaliumiodid</a> in <a href="Methanol" title="Methanol">Methanol</a> in <a href="Cyclohexen" title="Cyclohexen">Cyclohexen</a> umgewandelt werden.<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>
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>1,2-Dibromcyclohexan kann zur <a href="Alkylierung" title="Alkylierung">Alkylierung</a> von <a href="Dicarbonyl" class="mw-redirect" title="Dicarbonyl">Dicarbonylverbindungen</a> verwendet werden.<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>
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-TCI-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-TCI_1-0">a</a></sup> <sup><a href="#cite_ref-TCI_1-1">b</a></sup> <sup><a href="#cite_ref-TCI_1-2">c</a></sup> <sup><a href="#cite_ref-TCI_1-3">d</a></sup> <sup><a href="#cite_ref-TCI_1-4">e</a></sup> <sup><a href="#cite_ref-TCI_1-5">f</a></sup> <sup><a href="#cite_ref-TCI_1-6">g</a></sup></span> <span class="reference-text">Eintrag zu <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.tcichemicals.com/eshop/de/de/commodity/D2410">(±)-trans-1,2-Dibromocyclohexane, >95.0%</a></span> bei TCI Europe, abgerufen am 30. September 2023.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-S._Coffey-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-S._Coffey_2-0">a</a></sup> <sup><a href="#cite_ref-S._Coffey_2-1">b</a></sup> <sup><a href="#cite_ref-S._Coffey_2-2">c</a></sup> <sup><a href="#cite_ref-S._Coffey_2-3">d</a></sup></span> <span class="reference-text">S. Coffey: <cite style="font-style:italic">Including the Official Reports of a Number of Learned Societies</cite>. Elsevier Science, ISBN 978-1-4832-2387-2, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>33</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=coPNCgAAQBAJ&pg=PA33#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:1%2C2-Dibromcyclohexan&rft.au=S.+Coffey&rft.btitle=Including+the+Official+Reports+of+a+Number+of+Learned+Societies&rft.genre=book&rft.isbn=9781483223872&rft.pages=33&rft.pub=Elsevier+Science" style="display:none"> </span></span>
</li>
<li id="cite_note-Richard_Montgomery_Stephenson-3"><span class="mw-cite-backlink"><a href="#cite_ref-Richard_Montgomery_Stephenson_3-0">↑</a></span> <span class="reference-text">Richard Montgomery Stephenson, Stanisław Malanowski: <cite style="font-style:italic">Handbook of the Thermodynamics of Organic Compounds</cite>. Springer Netherlands, 2012, ISBN 978-94-009-3173-2, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>191</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=X9PsCAAAQBAJ&pg=PA191#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:1%2C2-Dibromcyclohexan&rft.au=Richard+Montgomery+Stephenson%2C+Stanis%C5%82aw+Malanowski&rft.btitle=Handbook+of+the+Thermodynamics+of+Organic+Compounds&rft.date=2012&rft.genre=book&rft.isbn=9789400931732&rft.pages=191&rft.pub=Springer+Netherlands" style="display:none"> </span></span>
</li>
<li id="cite_note-Janice_Smith-4"><span class="mw-cite-backlink"><a href="#cite_ref-Janice_Smith_4-0">↑</a></span> <span class="reference-text">Janice Smith: <cite style="font-style:italic">Ebook: Organic Chemistry</cite>. McGraw-Hill Education, 2014, ISBN 978-0-07-717185-8, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>408</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=T6RvEAAAQBAJ&pg=PA408#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:1%2C2-Dibromcyclohexan&rft.au=Janice+Smith&rft.btitle=Ebook%3A+Organic+Chemistry&rft.date=2014&rft.genre=book&rft.isbn=9780077171858&rft.pages=408&rft.pub=McGraw-Hill+Education" style="display:none"> </span></span>
</li>
<li id="cite_note-Michael_B._Smith-5"><span class="mw-cite-backlink"><a href="#cite_ref-Michael_B._Smith_5-0">↑</a></span> <span class="reference-text">Michael B. Smith, Jerry March: <cite style="font-style:italic">March's Advanced Organic Chemistry</cite>. Wiley, 2007, ISBN 0-470-08494-4, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>1011</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=by05kNKm_xYC&pg=PA1011#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:1%2C2-Dibromcyclohexan&rft.au=Michael+B.+Smith%2C+Jerry+March&rft.btitle=March%27s+Advanced+Organic+Chemistry&rft.date=2007&rft.genre=book&rft.isbn=0470084944&rft.pages=1011&rft.pub=Wiley" style="display:none"> </span></span>
</li>
<li id="cite_note-P.S._Kalsi-6"><span class="mw-cite-backlink"><a href="#cite_ref-P.S._Kalsi_6-0">↑</a></span> <span class="reference-text">P.S. Kalsi: <cite style="font-style:italic">Stereochemistry & Mechanism Through solved Problems</cite>. New Age International, ISBN 978-81-224-1177-5, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>93</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=LVKQC5spUNwC&pg=PA93#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:1%2C2-Dibromcyclohexan&rft.au=P.S.+Kalsi&rft.btitle=Stereochemistry+%26+Mechanism+Through+solved+Problems&rft.genre=book&rft.isbn=9788122411775&rft.pages=93&rft.pub=New+Age+International" style="display:none"> </span></span>
</li>
<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">G. Kainz: <cite style="font-style:italic">Über eine spektroskopische Konformationsanalyse von trans-1,2-Dichlorcyclohexan bzw. trans-1,2-Dibromcyclohexan</cite>. In: <cite style="font-style:italic">Fresenius' Zeitschrift für analytische Chemie</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>164</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>3</span>, 1958, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>367–367</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/10.1007/BF00455817">10.1007/BF00455817</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:1%2C2-Dibromcyclohexan&rft.atitle=%C3%9Cber+eine+spektroskopische+Konformationsanalyse+von+trans-1%2C2-Dichlorcyclohexan+bzw.+trans-1%2C2-Dibromcyclohexan&rft.au=G.+Kainz&rft.date=1958&rft.doi=10.1007%2FBF00455817&rft.genre=journal&rft.issue=3&rft.jtitle=Fresenius%27+Zeitschrift+f%C3%BCr+analytische+Chemie&rft.pages=367-367&rft.volume=164" style="display:none"> </span></span>
</li>
<li id="cite_note-Metin_Balcı-8"><span class="mw-cite-backlink"><a href="#cite_ref-Metin_Balcı_8-0">↑</a></span> <span class="reference-text">Metin Balcı: <cite style="font-style:italic">Reaction Mechanisms in Organic Chemistry</cite>. Wiley, 2021, ISBN 978-3-527-83459-4, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>109</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=BbVQEAAAQBAJ&pg=PA109#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:1%2C2-Dibromcyclohexan&rft.au=Metin+Balc%C4%B1&rft.btitle=Reaction+Mechanisms+in+Organic+Chemistry&rft.date=2021&rft.genre=book&rft.isbn=9783527834594&rft.pages=109&rft.pub=Wiley" style="display:none"> </span></span>
</li>
<li id="cite_note-9"><span class="mw-cite-backlink"><a href="#cite_ref-9">↑</a></span> <span class="reference-text"><cite style="font-style:italic">Including the Official Reports of a Number of Learned Societies</cite>. Elsevier Science, ISBN 978-1-4832-2387-2, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>35</span> (<a rel="nofollow" class="external text" href="https://books.google.de/books?id=coPNCgAAQBAJ&pg=PA35#v=onepage">eingeschränkte Vorschau</a> in der Google-Buchsuche).<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:1%2C2-Dibromcyclohexan&rft.btitle=Including+the+Official+Reports+of+a+Number+of+Learned+Societies&rft.genre=book&rft.isbn=9781483223872&rft.pages=35&rft.pub=Elsevier+Science" style="display:none"> </span></span>
</li>
<li id="cite_note-10"><span class="mw-cite-backlink"><a href="#cite_ref-10">↑</a></span> <span class="reference-text">N. S. Sadykhov, Sh. S. Nasibov, F. M. Muradova, R. A. Gasymov: <cite style="font-style:italic">Alkylation of β-dicarbonyl compounds with 1,2-dibromocyclohexane</cite>. In: <cite style="font-style:italic">Russian Chemical Bulletin</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>47</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>2</span>, 1998, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>310–312</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/10.1007/BF02498956">10.1007/BF02498956</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:1%2C2-Dibromcyclohexan&rft.atitle=Alkylation+of+%CE%B2-dicarbonyl+compounds+with+1%2C2-dibromocyclohexane&rft.au=N.+S.+Sadykhov%2C+Sh.+S.+Nasibov%2C+F.+M.+Muradova%2C+...&rft.date=1998&rft.doi=10.1007%2FBF02498956&rft.genre=journal&rft.issue=2&rft.jtitle=Russian+Chemical+Bulletin&rft.pages=310-312&rft.volume=47" style="display:none"> </span></span>
</li>
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