Regioselective free radical phenylsulfenation of a non-activated delta-carbon atom by the photolysis of alkyl benzenesulfenate

Abstract

A regioselective free radical introduction of a phenylthio group onto a non-activated delta-carbon atom was achieved by photolysis of alkyl benzenesulfenates in the presence of hexabutylditin, and delta-phenylthio alcohols were obtained in 35-91% yields. delta-Phenylsulfenylation of a non-activated carbon atom induced only by irradiation of alkyl benzenesulfenates (without initiation by hexabutylditin) also occurs, however, slower reaction rates were observed and lower yields of delta-phenylthio alcohols were obtained. (C) 2002 Published by Elsevier Science Ltd.