Aryl-substituted sulfonium betaines: preparation and use in the epoxidation of aldehydes

J Org Chem. 2006 Oct 13;71(21):8287-90. doi: 10.1021/jo061370u.

Abstract

Thermally induced decarboxylation of carboxymethylsulfonium betaines results in formation of the corresponding sulfur ylides in situ. Decarboxylation rates for a range of arylcarboxymethylsulfonium betaine salts have been determined using NMR spectroscopy, and the efficiency of ylide generation and trapping has been evaluated via methylidene transfer to a range of aldehydes to form epoxides.