The reactions of some α-halo-β-ketosulfones with hard and soft nucleophiles. A preparation of sulfinate esters

JS Grossert, PK Dubey…

Index: Grossert, J. Stuart; Dubey, Pramod K.; Elwood, Tom Canadian Journal of Chemistry, 1985 , vol. 63, p. 1263 - 1267

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Citation Number: 21

Abstract

The α-halo-β-ketosulfonyl functionality was attacked by ethanethiolate at the halogen which, in the presence of a proton source, usually resulted in reduction to the β-ketosulfone. A range of other soft nucleophiles did not react, whereas hard nucleophiles invariably attacked at the carbonyl, with subsequent cleavage to α-halosulfones. Ambident arylsulfinate anions usually attacked at halogen to form the sulfonyl halide, which reacted with excess sulfinate ...