Oxepin

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.

Oxepin

Names
Preferred IUPAC name Oxepine
Other names Oxacycloheptatriene
Identifiers
CAS Number	291-70-3 Y
3D model (JSmol)	Interactive image
ChemSpider	4953942 Y
PubChem CID	6451477
UNII	CVP5X85XX5 Y
CompTox Dashboard (EPA)	DTXSID10183353
InChI InChI=1S/C6H6O/c1-2-4-6-7-5-3-1/h1-6H N Key: ATYBXHSAIOKLMG-UHFFFAOYSA-N 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	94.113 g·mol−1
Related compounds
Related compounds	Cyclohexene oxide Oxonane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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]

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

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