Chemistry:Oxepin

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Oxepin
Skeletal formula of oxepin
Ball-and-stick model of the oxepin molecule
Oxepin-based-on-xtal-3D-bs-17-side-view.png
Names
Preferred IUPAC name
Oxepine
Other names
Oxacycloheptatriene
Identifiers
3D model (JSmol)
ChemSpider
UNII
Properties
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).
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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-benzene oxide.png

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.

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

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. PMID 8354177.