Chemistry:Oxepine
From HandWiki
Oxepine 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 oxepine isomer, an orange liquid.[2]
In nature, oxepine is an intermediate in the oxidation of benzene by the cytochrome P450 (CYP).[3] Other arene oxides are metabolites of the parent arene.
Benzene oxides are produced in the laboratory from dehydrohalogenation of the corresponding dihaloepoxide:[4]
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. PMID 8354177.
- ↑ Gillard, J. R.; Newlands, M. J.; Bridson, J. N.; Burnell, D. J. (1991). "π-Facial stereoselectivity in the Diels–Alder reactions of benzene oxides". Canadian Journal of Chemistry 69 (9). doi:10.1139/v91-199.
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