Cyclopropanesulfonic acid

In the nucleophilic substitution reactions of alkylsulfonyl chlorides and ring-substituted benzylsulfonyl chlorides, the operation of two competing reaction pathways has been established (a) E-A (sulfene) mechanism and (b) direct nucleophilic substitution at sulfur (general base catalysis). The relative significance of these competing mechanisms depends on the nature of the substrate and the precise reaction conditions. In the hydrolysis of cyclopropane-sulfonyl chloride 11 with tertiary amines in organic media, the sulfene 12 appears to be the crucial intermediate in the formation of cyclopropanesulfonic acid 13 (Equation 12). ... 

Trimethylsilyl chlorosulfonate 459 is useful as a mild sulfonating agent and it reacts with a range of organic compounds containing the trimethylsilyl group as illustrated by Equations 144-146. " It was by this synthetic route that cyclopropanesulfonic acid 460 was first prepared (Equation 145). The general mechanism of these reactions is depicted in Scheme 14. 

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