The photochemistry of 2,3-bis(p-methoxyphenyl)oxirane: trapping of a C–C cleaved intermediate in an electron-transfer sensitised process

Abstract

2,3-Bis(p-methoxyphenyl)oxirane (6) rearranges, with C–O cleavage, to the carbonyl compounds (8) and (9) on irradiation, direct or triplet sensitised, and thermally: in contrast C–C cleavage is observed with dicyanoanthracene as electron-transfer sensitiser, and the resulting intermediate can be trapped by dipolarophiles in synthetically useful reactions.