Synthesis and Structure of Thioketones having alpha-Hydrogen and Corresponding Enethiols

Abstract

We report here, the synthesis and properties of alkyl-9-triptycylthioketones 1 as stable compounds of carbon-sulfur double bond carrying an alpha-hydrogen. Synthesis of thioketones 1 was performed by reaction of the corresponding hydrazones with S2Cl2. The isolated thioketones were thermally stable and the tautomerization to the enethiols was not observed in solution. The proton abstraction reaction of 1 with KH was easily proceeded to give the corresponding enethiolates. Quenching of the reaction mixture gave the stable enethiols 2. The reactivity of 1 and oxidation of 2 will also be discussed.