Abstract
Abstract In the presence of a catalytic amount of a tertiary amine, thionyl chloride generally oxidizes carboxylic acids1,2 and ketones1 at α carbon atoms to form α-chloro-α-chlorosulfenyl derivatives and their subsequent reaction products. Examination of reaction mixtures of thionyl chloride with a number of variously substituted 4-aryl-2-butanones revealed that in the case of the 3-methoxy or 3-hydroxy derivatives, cyclization onto the aromatic ring to form a benzo[b] thiophene competes quite favorably with cyclization onto enol to form a thietanone.4 The results were consistent only with thionyl chloride oxidation proceeding exclusively at the methylene position.
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