Rubber chemicals derived from conjugate addition. II. Synthesis of a novel class of benzoquinone diimines

Abstract

Various 2-alkylthio-5-amino- and 2,5-diamino-1,4-phenylenediamines were prepared by treatment of N-(1,3-dimethylbutyl)-N′-phenyl-1,4-quinonediimine with thiols and amines using air as an oxidizing agent. Key 2-alkylthio-1,4-benzoquinone diimines were prepared via Ag2O oxidation of the corresponding 1,4-phenylenediamines.