Canadian journal of chemistry

A brief survey of the use of the Pummerer rearrangement for the alkylation of 1, 3-oxathiolan-5-ones and 1, 3-thiazolidin-4-ones

JM McIntosh, RK Leavitt

Index: McIntosh, John M.; Leavitt, Randy K. Canadian Journal of Chemistry, 1985 , vol. 63, p. 3313 - 3316

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Citation Number: 12

Abstract

Oxidation of 1, 3-oxathiolan-5-ones (1) gives acceptable yields of sulfoxides only when C4 is unsubstituted. Sulfoxides derived from 1, 3-thiazolidine-4-ones (8) are easily prepared. Acid- catalyzed rearrangement in the presence of 1-alkenes or benzene leads to alkylation (arylation) at C5. Alkylation of 8 c may be generally more effective than that of 1. An aldol condensation of 8 c shows little stereoselectivity.