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]
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
^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.
^Paquette, Leo A.; Barrett, J. H. (1969). "2,7-Dimethyloxepin". Org. Synth. 49: 62. doi:10.15227/orgsyn.049.0062.
^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.
