Preparation of allenic sulfones and allenes from the selenosulfonation of acetylenes

…, MV Krishna, KR Muralidharan

Index: Back, Thomas G.; Krishna, M. Vijaya; Muralidharan, K. Raman Journal of Organic Chemistry, 1989 , vol. 54, # 17 p. 4146 - 4153

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Citation Number: 29

Abstract

P-(Phenylse1eno) vinyl sulfones 2 are readily obtained from the free-radical selenosulfonation of acetylenes. Compounds 2 isomerize to allyl sulfones 4 under base- catalyzed conditions in nearly quantitative yield, with high stereoselectivity favoring the 2 configuration. Allyl sulfones 4 afford generally high yields of allenic sulfones 1 when subjected to oxidation with m-chloroperbenzoic acid or tert-butyl hydroperoxide, followed ...

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