One-Step Synthesis of Acetylenes from Ketones

Abstract

The classical route to acetylenes from ketones involves the formation of gem-dichlorides or vinyl chlorides followed by elimination of hydrogen chloride with alkali hydroxides or amides.¹ The use of these latter reagents is evidently incompatible with compounds having other functional groups which are sensitive to strong bases. A need to preserve a carboxylic ester present in the same molecule in which a methyl ketone is to be transformed into the ethynyl moiety led us to investigate the modification of the dehydrochlorination process, and we wish to communicate our preliminary findings.