A New Pathway for Cleavage of Some Phenacyl and Styryl Thioethers

Article abstract of DOI:10.1021/jo00154a017

Ultraviolet photolysis or preparative electroreduction of 1-(benzylthio)-2-phenyl-2-propene results in both C-S and C-C bond cleavages.The analogous methyl thioether is nearly inert photochemically and does not give monomeric products upon electroreduction.The phenyl thioether gives exclusively C-S fragmentation.A mechanism involving photoinduced electron transfer followed by cleavage of the zwitterionic diradical is proposed for the novel C-C cleavage.Electrochemical peak potentials for the series of phenacyl and styryl thioethers are reported.