Synthesis of Dibutadienyl Piperazines, 1,1-Dithio and 1,4-Dithio Substituted Dienes from Nitrodienes

Nitrodiene 1a , 1b reacted with 1,4-dithiolbutan and gave the heterocyclic compounds 3a , 3b . 1b gave with 1,3-acetonedithiol the compound 5b . The nitrodiene compound 1b reacted with o-dithiolbenzene ( 6 ) and yielded the ketene dithioacetal ( 7b ). Heterocyclic compounds 11a , 11b , 12a , and 12b were prepared from the reactions of 9a with 2,2'-oxydiethanethiol. The compounds 9a , 9b were prepared from 2-nitropentachloro-1,3-butadiene and alkylthiols ( 8a , 8b ). Mono(thio) substituted diene compound 9b gave dibutadienyl piperazine 14b with piperazine in diethylether.