SYNTHESIS OF HETEROCYCLIC COMPOUNDS AND NEW ROUTES FOR THE PREPARATION OF CERTAIN DITHIOCARBONATES AND SULFIDES FROM POTASSIUM CYANODITHIOIMIDOCARBONATE^1,2

Abstract

The reaction of potassium cyanodithioimidocarbonate with 3-chloro-2,4-pentanedione, ethyl α-chloroacetoacetate, chloroacetone, or 2,3-dichloro 1,4-napthoquinone afforded novel heterocyclic compounds (2), (3), and (4) and (6). The reaction of the potassium salt with p-chlorophenyl chlorothioformate, 4-chloro-3-nitro or 3,5-dinitrobenzotrifluoride or dimethylthiocarbamoyl chloride furnished new routes for the synthesis of S,S′-bis-p-chlorophenyl dithiocarbonate (7) and the sulfides (8), (9) and (10). Possible mechanisms and supporting NMR and mass spectra are discussed.