{{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<br/>Oxonane }} }}

'''Oxepine''' is an oxygen-containing heterocycle consisting of a seven-membered ring with three double bonds. The parent C<sub>6</sub>H<sub>6</sub>O exists as an equilibrium mixture with '''benzene oxide'''. center|200px

The oxepin–benzene oxide equilibrium is affected by the ring substituents.<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 by the cytochrome P450 (CYP).<ref name=Tox /> Other arene oxides 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 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