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Oxepin

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(Redirected from Benzene oxide)
Oxepin
Skeletal formula of oxepin
Ball-and-stick model of the oxepin molecule
Names
Preferred IUPAC name Oxepine
Other names Oxacycloheptatriene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H6O/c1-2-4-6-7-5-3-1/h1-6HKey: ATYBXHSAIOKLMG-UHFFFAOYSA-N
  • InChI=1/C6H6O/c1-2-4-6-7-5-3-1/h1-6HKey: ATYBXHSAIOKLMG-UHFFFAOYAS
SMILES
  • C1=CC=COC=C1
Properties
Chemical formula C6H6O
Molar mass 94.113 g·mol
Related compounds
Related compounds Cyclohexene oxide
Oxonane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. A related dimethyl derivative exists mainly as the oxepin isomer, an orange liquid.

Oxepin is an intermediate in the oxidation of benzene by the cytochrome P450 (CYP). 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. JSTOR 3431535. PMC 1519582. PMID 8354177.
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