The preparation and characterization of 5-substituted-4-chloro-1,2,3-dithiazolium salts and their conversion into 4-substituted-3-chloro-1,2,5-thiadiazoles.
A series of monosubstituted acetonitriles were treated with disulfur dichloride at room temperature in CH2Cl2 to afford 5-substituted-4-chloro-1,2,3-dithiazolium chlorides 1. Where the 5-substituent was not a good leaving group the chloride salts were converted into the corresponding perchlorate salts 2 which were sufficiently stable and soluble to provide both (1)H- and (13)C-NMR and cyclic voltammetry data. Several of the dithiazolium chlorides were converted into their corresponding 4-substituted-3-chloro-1,2,5-thiadiazoles 13 on treatment with aqueous ammonia. Mechanisms for all reactions are proposed.
Koutentis
Panayiotis A
PA
Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus. koutenti@ucy.ac.cy
D000097:Acetonitriles / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000138:chemical synthesis* / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D008954:Models, Biological; D012492:Salts / Q000737:chemistry; D013457:Sulfur Compounds / Q000737:chemistry; D013830:Thiadiazoles / Q000138:chemical synthesis*
D000097:Acetonitriles; D002712:Chlorides; D006571:Heterocyclic Compounds; D012492:Salts; D013457:Sulfur Compounds; D013830:Thiadiazoles