# Oxepine

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Oxepine
> Markdown URL: https://mediated.wiki/source/Oxepine.md
> Source: https://en.wikipedia.org/wiki/Oxepine
> Source revision: 1339219805
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 448773926
| ImageFileL1 = Oxepine.svg
| ImageSizeL1 = 110
| ImageAltL1 = Skeletal formula of oxepin
| ImageFileR1 = Oxepin-based-on-xtal-3D-bs-17.png
| ImageSizeR1 = 140
| ImageAltR1 = Ball-and-stick model of the oxepin molecule
| ImageFile2 = Oxepin-based-on-xtal-3D-bs-17-side-view.png
| ImageSize2 = 140
| PIN=Oxepine
| OtherNames=Oxacycloheptatriene
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=291-70-3
| PubChem=6451477
| SMILES=C1=CC=COC=C1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = CVP5X85XX5 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4953942
| InChI = 1/C6H6O/c1-2-4-6-7-5-3-1/h1-6H
| InChIKey = ATYBXHSAIOKLMG-UHFFFAOYAS
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C6H6O/c1-2-4-6-7-5-3-1/h1-6H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = ATYBXHSAIOKLMG-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=6 | H=6 | O=1
}}
| Section8 = {{Chembox Related
| OtherCompounds = [Cyclohexene oxide](/source/Cyclohexene_oxide)<br/>[Oxonane](/source/Oxonane)
}}
}}

'''Oxepine''' is an [oxygen](/source/oxygen)-containing [heterocycle](/source/heterocycle) consisting of a seven-membered [ring](/source/ring_(chemistry)) with three [double bond](/source/double_bond)s. The parent C<sub>6</sub>H<sub>6</sub>O exists as an [equilibrium](/source/chemical_equilibrium) mixture with '''benzene oxide'''.
center|200px

The oxepin–benzene oxide equilibrium is affected by the ring [substituent](/source/substituent)s.<ref name=TautHist /> A related dimethyl derivative exists mainly as the oxepine isomer, an orange liquid.<ref name=Me2Synth />

In nature, oxepine is an intermediate in the oxidation of [benzene](/source/benzene) by the [cytochrome P450](/source/cytochrome_P450) (CYP).<ref name=Tox />  Other [arene oxide](/source/arene_oxide)s are metabolites of the parent arene.
:360px|Formation and selected reactions of benzene oxide (2) and oxepin (3)

Benzene oxides are produced in the laboratory from [dehydrohalogenation](/source/dehydrohalogenation) of the corresponding dihaloepoxide:<ref>{{cite journal|first1=J.&nbsp;R.|last1=Gillard|first2=M.&nbsp;J.|last2=Newlands|first3=J.&nbsp;N.|last3=Bridson|first4=D.&nbsp;J.|last4=Burnell|title=π-Facial stereoselectivity in the Diels–Alder reactions of benzene oxides|year=1991|journal=Canadian Journal of Chemistry|volume=69|issue=9|pp=1337–1343|doi=10.1139/v91-199|doi-access=free}}</ref>
:frameless|upright=1|Oxepin synthesis

==References==
<references>
<ref name=Me2Synth>{{cite journal|title=2,7-Dimethyloxepin|first1=Leo&nbsp;A.|last1=Paquette |author1-link= Leo Paquette |first2=J.&nbsp;H. |last2=Barrett|journal=Org. Synth.|year=1969|volume=49|page=62|doi=10.15227/orgsyn.049.0062|doi-access=free}}</ref>
<ref name=Tox>{{cite journal |doi=10.1289/ehp.93100293 |journal=Environmental Health Perspectives |title=The Toxicology of Benzene |volume=100 |pages=293–306 |first1=R.|last1=Snyder |first2= G. |last2=Witz |first3= B.&nbsp;D. |last3=Goldstein |year=1993 |pmc=1519582 |pmid=8354177|jstor=3431535 |doi-access=free}}</ref>
<ref name=TautHist>{{cite journal | doi = 10.1002/anie.196703851 | journal = Angewandte Chemie International Edition in English | title=Benzene Oxide–Oxepin Valence Tautomerism| volume=6 |issue=5 |pages =385–401 |first1=E.|last1=Vogel |first2=H.|last2=Günther | year = 1967}}</ref>
</references>

{{Commons category|Oxepin}}
Category:Oxepines

---
Adapted from the Wikipedia article [Oxepine](https://en.wikipedia.org/wiki/Oxepine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Oxepine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.