Reaction of 1,4,2-Dithiazolium Salts with Amino Compounds

Article abstract of DOI:10.1246/bcsj.61.4043

Systematic studies on the behavior of 1,4,2-dithiazolium cations (1) toward various amino compounds (ammonia, aliphatic and aromatic amines, hydrazine, semicarbazide, thiosemicarbazide derivatives, etc.) were performed.The reaction pathway could be classified into three types depending on possibile three fission modes of the initially-formed adduct.The main products were 5-imino-1,4,2-dithiazole, thiourea, and 1,3,4-thiadiazole derivatives, through the three different pathways, respectively.In order to clarify the factors controlling the reaction courses, the reactions of 1 with p-substituted aniline derivatives were carried out under systematically varying conditions.The strength of bases and the polaritiy of solvents had clear influence on the reactivity.The reaction mechanism is also discussed.