The photochemical reaction between diazomethane and 1,2-epoxypropane

Abstract

Photolysis of diazomethane in the presence of 1,2-epoxypropane leads to the formation of higher homologues (1,2-epoxybutane and 2,3-epoxybutane) and of acetone. The former would follow from the insertion reactions of carbene but may involve the direct reaction of excited diazomethane. Energy transfer from excited diazomethane to propylene oxide followed by rearrangement is suggested as a mechanism for the production of acetone.