Mechanism for the formation of N,N'-bis(phenylthio)quinodiimide from phenylsulfenyl chloride and 1,4-phenylenediamine

Abstract

A mechanism was proposed for the formation of N,N'-bis(phenylthio)quinodiimide (BPTQD) as a series of one-electron oxidation-reduction reactions of intermediate derivatives of 1,4-phenylenediamine (PDA) with phenylsulfenyl chloride (PSC) as the oxidizing agent. A change in the ratio of the starting reagents in accord with the proposed mechanism gives a doubled yield of BPTQD. Diphenyl disulfide and chloro-derivatives of BPTQD are formed as by-products.