Dimethyloxosulfonium methylide ((CH3) 2SOCH2) and dimethylsulfonium methylide ((CH3) 2SCH2). Formation and application to organic synthesis

EJ Corey, M Chaykovsky

Index: Corey,E.J.; Chaykovsky,M. Journal of the American Chemical Society, 1965 , vol. 87, p. 1353 - 1364

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Citation Number: 1373

Abstract

The generation of dimethyloxosulfonium methylide (11) and dimethylsulfonium methylide (XIII) as reactive intermediates is described. Both ylides are nucleophiles and both function to transfer methylene to certain electrophilic unsaturated linkages, including CEO, C= N, C= S, and in certain cases C= C. The less reactive oxosulfonium ylide interacts with the carbonyl function of aromatic and nonconjugated aldehydes and ketones to form oxiranes ...