On the reaction of chlorodithiophosphoric acid pyridiniumbetaine with polyfunctional nucleophiles: Part II. Reaction with thiosemicarbazide derivatives

Abstract

Chlorodithiophosphoric acid pyridiniumbetaine, PyPS 2Cl ( I), reacts with thiosemicarbazide derivatives (RNH)(H 2NNMe)CS, R= iso-propyl, tert-butyl, in acetonitrile in the absence of any HCl-acceptor to form new compounds with a five-membered heterocycle, i.e. 5- iso-propylamino-4-methyl-2-sulfido-2-thioxo-1,3,4,2λ 5-thiadiazaphospholan-5-onium ( II) or 5- tert-butylamino-4-methyl-2-sulfido-2-thioxo-1,3,4,2λ 5-thiadiazaphospholan-5-onium ( III). The triethylammonium salt of 1,3-bis-( N-methyl- N′- tert-butyl-thioureido)-2,4-disulfido-2,4-dithioxo-1,3-diaza-2λ 5,4λ 5-diphosphetidine ( IV) is formed when the reaction is carried out in the presence of triethylamine. The prepared compounds were characterized by 31P NMR, FT-IR spectroscopies, mass spectrometry and the molecular structures of II, III and IV were determined by X-ray crystallography.