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

, : Aryl-substituted sulfonium betaines: preparation and use in the epoxidation of aldehydes. Journal of Organic Chemistry 71(21): 8287-8290

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.


PMID: 17025328

DOI: 10.1021/jo061370u

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