Regioselective free radical phenylsulfenation of a non-activated delta-carbon atom by the photolysis of alkyl benzenesulfenate
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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.
Keywords:radicals and radical reactions / 1,5-hydrogen migration / intramolecular fuctionalization / sulfenic acids and derivatives / sulfides / delta-phenylthio alcohols
Source:Tetrahedron, 2003, 59, 2, 187-196
- Pergamon-Elsevier Science Ltd, Oxford