New N,S-substituted diene compounds from reactions of mono(arylthio)-substituted polyhalo-2-nitrodienes with amines

Abstract

S-mono to S,S-tetrasubstituted 1,3-nitrodiene compounds 3-6 have been obtained from the reaction of 2-nitropentahalobutadiene with p-methylthiophenol. Mono(thio)substituted diene compound 3 gives dibutadienyl piperazine 10 with piperazine in diethylether, and compounds 12a and 12b with piperazine derivatives. From 3, compounds 14a-h, with primary amines, and compounds 8a-c with secondary amines, are achieved. 16 was obtained from the reaction of compound 3 with p-phenylene diamine in CH2Cl2.