Oxepin

Oxepin
Skeletal formula of oxepin
Ball-and-stick model of the oxepin molecule
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 ☒N
    Key: ATYBXHSAIOKLMG-UHFFFAOYSA-N ☒N
  • InChI=1/C6H6O/c1-2-4-6-7-5-3-1/h1-6H
    Key: ATYBXHSAIOKLMG-UHFFFAOYAS
  • C1=CC=COC=C1
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.

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).
  1. ^ Cite error: The named reference TautHist was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference Me2Synth was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference Tox was invoked but never defined (see the help page).