Formation of bis-[α-(arylhydrazono)aralkyl] disulphides from N-aryl-N′-thioaroylhydrazines and sulphonyl chlorides, and related topics

Abstract

The reaction of N-aryl-N′-thioaroylhydrazines (I) with various alkane-, arylalkane-, and arene-sulphonyl chlorides in the presence of triethylamine gave the bis-[α-(arylhydrazono)aralkyl] disulphides (III) and N-aryl-N-alkyl(or aryl)sulphonyl-N′-thioaroylhydrazines (IV), together with the sulphinate ion derived from the sulphonyl chloride, the ratio depending on the relative concentration of the reactants and the substituents present in the sulphonyl chloride. Similar reactions [of (ID)] with benzenesulphinyl and 2-nitrobenzenesulphenyl chlorides gave the disulphide (IIID). The disulphides (III) were also formed by reaction between compounds of types (I) and (IV) in the presence of triethylamine. Compounds (IV) alone gave the disulphides in refluxing ethanol, but in refluxing acetonitrile–triethylamine (1 : 1) they afforded the corresponding bis-[α-(arylhydrazono)aralkyl] sulphides (VII).