SYNTHETIC EXPLOITATION OF THE RING-OPENING OF 3,4-DINITROTHIOPHENE. A NOVEL ACCESS TO 1,4-DIALKYL- AND 1,4-DIARYL-2,3-DINITRO-1,3-BUTADIENES

Article abstract of DOI:10.1016/S0040-4039(00)97773-6

(E,E)-1,4-Bis(diethylamino)-2,3-dinitro-1,3-butadiene (2a), obtained from the ring-opening of 3,4-dinitrothiophene, reacts with Grignard reagents in THF to give good yields of 1,4-disubstituted (Et, cy-Hex, Ph) 2,3-dinitro-1,3-butadienes (3a-c) having almost exclusively (E,E) configuration.