Synthesis, resolution and racemization studies of 1,2-epoxy-1,2-dihydrochrysene

Abstract

(+)-1,2-Epoxy-1,2-dihydrochrysene, a major initial mammalian metabolite of chrysene, has been synthesised and assigned the configuration (1R, 2S). Kinetic studies on the spontaneous thermal racemization of (+)-1,2-epoxy-1,2-dihydrochrysene gave a barrier to racemization (E_a) of 24.8 kcal mol^–1. The kinetic results and activation parameters support a thermal racemization mechanism involving an oxepin intermediate.