Oxepine
From Wikipedia, the free encyclopedia
(Redirected from Benzene oxide)
Oxepine
Names
Identifiers
Properties
Related compounds
Preferred IUPAC name
Oxepine
Other names
Oxacycloheptatriene
- 291-70-3 checkY
3D model (JSmol)
ChemSpider
- 4953942 checkY
UNII
- CVP5X85XX5 checkY
- InChI=1S/C6H6O/c1-2-4-6-7-5-3-1/h1-6H ☒NKey: ATYBXHSAIOKLMG-UHFFFAOYSA-N ☒N
- InChI=1/C6H6O/c1-2-4-6-7-5-3-1/h1-6HKey: ATYBXHSAIOKLMG-UHFFFAOYAS
- C1=CC=COC=C1
Molar mass
94.113 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
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
[edit ]- ^ 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.
- ^ 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): 1337–1343. doi:10.1139/v91-199 .
Wikimedia Commons has media related to Oxepin .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Oxepine&oldid=1339219805"