Thermal racemization of a chiral arene oxide metabolite: chrysene 3,4-oxide

Chrysene 3,4-oxide, a major initial mammalian metabolite of chrysene, now synthesised in optically active form and configurationally assigned, has been found to racemize thermally with an activation energy of 25·2 kcal mol–1, consistent with an earlier perturbational molecular orbital calculation-predicted oxepin intermediate mechanism.