Sulfur ylides via decarboxylation of carboxymethylsulfonium betaines: A novel and mild protocol for the preparation of oxiranes

A novel protocol for the generation of sulfur ylides is described. The overall process involves thermal decarboxylation of a carboxymethyl-sulfonium betaine to give a sulfur ylide that, in the presence of an aldehyde, affords the corresponding terminal oxirane. Yields were found to correlate with the electron deficiency of the aryl aldehyde. In situ generation of betaine in the presence of an aldehyde successfully afforded the desired oxirane in moderate yield, thus demonstrating the feasibility of a catalytic process.