Synthesis of some new S-, SS- and N,S-substituted 1,3-halonitrodienes

Abstract

Mono(thio) substituted butadiene compounds 3a-c are prepared by mixing 2-nitropentachlorobutadiene (1) with thiols (2a-c). 2-Nitrodiene 1 gives bis(thio)substituted 4a and 4d by the reaction with the same thiols in EtOH containing sodium hydroxide. N,S-Substituted 1,3-butadienes 6a-h were obtained by the reactions of 3a-c with primary amines. S-Substituted nitrodiene compounds 3a-c give 8a-c and 10a-c by the reaction with piperazines 7 and 9 in ether.