Palladium-Catalyzed Allylic Sulfinate-Sulfone Rearrangements

Abstract

Upon treatment with a zerovalent palladium catalyst, tetrakis(triphenylphosphine)palladium, in tetrahydrofuran under mild conditions allylic p-toluenesulfinates underwent a- or y-rearrange-ments of the sulfonyl group via ionic intermediates to give allylic sulfones. The regiochemistry of the rearrangements depends on the character of the intermediary allylic cationic carbons generated and the steric hindrance involved therein. © 1988, The Pharmaceutical Society of Japan. All rights reserved.