Oxepine

Oxepine
Names
	Preferred IUPAC name Oxepine
	Other names Oxacycloheptatriene
Identifiers
CAS Number	291-70-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	4953942 ;
PubChem CID	6451477;
UNII	CVP5X85XX5 ;
CompTox Dashboard (EPA)	DTXSID10183353 ;
	InChI 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;
	SMILES C1=CC=COC=C1;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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

^ 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.

[TautHist-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.

[Me2Synth-2] Paquette, Leo A.; Barrett, J. H. (1969). "2,7-Dimethyloxepin". Org. Synth. 49: 62. doi:10.15227/orgsyn.049.0062.

[Tox-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.

[4] 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.

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