Oxepin

Oxepin
Skeletal formula of oxepin	Ball-and-stick model of the oxepin molecule
Names
	IUPAC name Oxepine
	Other names Oxacycloheptatriene
Identifiers
CAS Number	291-70-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	4953942 ;
PubChem CID	6451477;
CompTox Dashboard (EPA)	DTXSID10183353 ;
	InChI InChI=1S/C6H6O/c1-2-4-6-7-5-3-1/h1-6H Key: ATYBXHSAIOKLMG-UHFFFAOYSA-N ; InChI=1/C6H6O/c1-2-4-6-7-5-3-1/h1-6H Key: ATYBXHSAIOKLMG-UHFFFAOYAS;
	SMILES C1=CC=COC=C1;
Properties
Chemical formula	C6H6O
Molar mass	94.11 g/mol
Related compounds
Related compounds	Cyclohexene oxide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Oxepin is an oxygen-containing heterocycle consisting of a seven-membered ring with three double bonds. The parent C₆H₆O exists as an equilibrium mixture with benzene oxide. The oxepin–benzene oxide equilibrium is affected by the ring substituents.[1] A related dimethyl derivative exists mainly as the oxepin isomer, an orange liquid.[2]

Formation and selected reactions of benzene oxide (2) and oxepin (3).

Oxepin is an intermediate in the oxidation of benzene by the cytochrome P450 (CYP).[3] Other arene oxides are metabolites of the parent arene.

References

E. Vogel, H. Günther (1967). "Benzene Oxide-Oxepin Valence Tautomerism". Angewandte Chemie International Edition in English. 6 (5): 385–401. doi:10.1002/anie.196703851.
L. A. Paquette and J. H. Barrett (1969). "2,7-Dimethyloxepin". Org. Synth. 49: 62. doi:10.15227/orgsyn.049.0062.CS1 maint: uses authors parameter (link)
R. Snyder, G. Witz, and B. D. Goldstein (1993). "The Toxicology of Benzene". Environmental Health Perspectives. 100: 293–306. doi:10.1289/ehp.93100293. JSTOR 3431535. PMC 1519582. PMID 8354177.CS1 maint: multiple names: authors list (link)

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[1] E. Vogel, H. Günther (1967). "Benzene Oxide-Oxepin Valence Tautomerism". Angewandte Chemie International Edition in English. 6 (5): 385–401. doi:10.1002/anie.196703851.

[2] L. A. Paquette and J. H. Barrett (1969). "2,7-Dimethyloxepin". Org. Synth. 49: 62. doi:10.15227/orgsyn.049.0062.CS1 maint: uses authors parameter (link)

[3] R. Snyder, G. Witz, and B. D. Goldstein (1993). "The Toxicology of Benzene". Environmental Health Perspectives. 100: 293–306. doi:10.1289/ehp.93100293. JSTOR 3431535. PMC 1519582. PMID 8354177.CS1 maint: multiple names: authors list (link)