The Preparation and Characterization of 5-Substituted-4-chloro-123-dithiazolium Salts and their Conversion into 4-Substituted-3-chloro-125-thiadiazoles

摘要

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 ¹H- and ¹³C-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.