Photochemical 1, 3-Addition of Anisole to Olefins. Synthetic Aspects

Abstract

Anisole undergoes photochemical 1, 3-addition to a variety of olefins with about the quantum efficiency of benzene but in considerably greater chemical yield. The latter feature may resuit from the stability of the adducts to continued irradiation. A 1, 3 photoadduct of an aromatic compound (anisole) to cyclohexene has been isolated for the first time. All of the 1, 3 adducts rearrange readily on treatment with acid to derivatives of bicyclo[3.2.1]oct-2-en-8-one. © 1977, American Chemical Society. All rights reserved.