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The reaction of the dianion of phenylsulfinylacetone with alkyl halides afforded beta-keto sulfoxides, which were first chlorinated with hexachloroethane and then treated successively with KH and t-BuLi to give carboxylic acids in three-steps in moderate overall yields from the alkyl halides. This procedure affords a good method for a synthesis of carboxylic acids from alkyl halides with three-carbon elongation.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Dianion of Sulfinylacetone as a Synthetic Equivalent of .BETA.-Enolate of Propionic Acid: A Novel Synthesis of Carboxylic Acids from Alkyl Halides with Three-Carbon Elongation