Reaction of olefins with Se-phenyl (selenothioperoxy)benzoate: a new anti-Markownikoff benzeneselenenylation

Abstract

A novel free radical addition of Se-phenyl (selenothioperoxy)benzoate (1) to a variety of olefins is described. The addition of selenosulphide (1) to terminal olefins proceeds regiospecifically to give the anti-Markownikoff benzeneselenenylated adducts. The addition to cycloalkenes gives a mixture of cis and trans isomers. These reactions provide a useful method for simultaneous introduction of phenylseleno and thiobenzoyloxy groups into a molecule. Oxidation–elimination of the phenylseleno group of the adducts gives vinyl thiobenzoates and/or allyl thiobenzoates.