Reaction of O-silylated enolates of carboxylic esters with benzyne. A convenient route to ortho-alkylbenzoic acids

SM Ali, S Tanimoto

Index: Ali, Syed Masarrat; Tanimoto, Shigeo Journal of the Chemical Society, Chemical Communications, 1988 , # 22 p. 1465 - 1466

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Abstract

The reaction of U-silylated enolates of carboxylic esters with benzyne proceeds smoothly to afford ortho-a1 kyl benzoic acids in moderate yields. ... A variety of reactions using 0-silylated enolates (1) of carboxylic esters have been documented. 1 In most cases, the nucleophilicity of their a-carbon causes the reactions with numerous electrophiles. Also, in a few cases, the formation of an intermediate radical containing trivalent a-carbon has been proposed.* Here we ...