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Paper | Special issue | Vol 70, No. 1, 2006, pp.519-530
Published online, 21st November, 2006
DOI: 10.3987/COM-06-S(W)56
Alkylation of 2-Butyl-4,4-dimethyl-4H-benzo[d][1,3]oxathiien-1,1-dioxide, a New Class of Acyl Anion Equivalents as an Alternative to Dithianes

Robert K. Boeckman, Jr.,* Susan M. Hanson, and Jeremy A. Cody

*Department of Chemistry, University of Rochester, University of Rochester, U.S.A.

Abstract

(2-Butyl-4,4-dimethyl-4H-benzo[d][1,3]oxathiine-1,1-dioxide has been found to react with several electrophiles, such as various halides and aldehydes, upon regioselective deprotonation. This method utilizes the sulfone group to form new carbon-carbon bonds while serving as a masked carbonyl. Subsequent hydrolysis of the sulfone provides a facile approach toward many useful synthetic intermediates. This methodology could provide a useful alternative to the use of dithiane groups.