Reactions of 3-hydroxyvinyl selenones with alkoxides. Oxetane formation and fragmentation reactions

M Shimizu, R Ando, I Kuwajima

Index: Shimizu, Makoto; Ando, Ryoichi; Kuwajima, Isao Journal of Organic Chemistry, 1984 , vol. 49, # 7 p. 1230 - 1238

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Citation Number: 50

Abstract

The initial or primary reaction of organosulfur 1-3 under pyrolytic conditions, is homolytic cleavage of the C-SO, bond (eq 1). The order of reactivity was observed to be sulfoxide>> sulfone> sulfide as predicted on the basis of the relative stabilities of the radicals produced. These sulfur and carbon radicals combine regioselectivity to form new sulfur-sulfur and carbon-carbon bonds (eq 2 and 3, respectively).