Competitive epoxidation and quinone formation in the dimethyldioxirane oxidation of diazoquinones as ambident nucleophiles

Abstract In addition to the expected dimethyldioxirane (DMD) oxidation of diazoquinones 1 to their quinones 2 , the corresponding epoxy quinones 3 are formed directly and not as secondary overoxidation products of the quinones 2 since the latter are persistent towards DMD under these conditions; this novel oxidation is rationalized in terms of the ambident nucleophilic nature of the diazoquinones and corroborated by MO (AM1) calculations.