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Topic summary

Oxepine

Oxepine
Names Preferred IUPAC name
Oxepine
Other names
Oxacycloheptatriene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C6H6O/c1-2-4-6-7-5-3-1/h1-6H
    Key: ATYBXHSAIOKLMG-UHFFFAOYSA-N
  • InChI=1/C6H6O/c1-2-4-6-7-5-3-1/h1-6H
    Key: ATYBXHSAIOKLMG-UHFFFAOYAS
  • C1=CC=COC=C1
Properties C6H6OMolar mass94.113 g·mol Related compounds
Related compounds
Cyclohexene oxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. A related dimethyl derivative exists mainly as the oxepine isomer, an orange liquid.

In nature, oxepine is an intermediate in the oxidation of benzene by the cytochrome P450 (CYP). Other arene oxides are metabolites of the parent arene.

Benzene oxides are produced in the laboratory from dehydrohalogenation of the corresponding dihaloepoxide:

Wikipedia source