Nechai, NI; Potkin, VI; Kaberdin, RV
Reactions of tetrachloro-1,3-dinitro-1,3-butadiene with strongly basic amines, such as tert-butylamine, piperidine, and morpholine, result in replacement of two terminal chlorine atoms in the β,β-dichloro-α-nitrovinyl moiety with formation of the corresponding dinitrodienediamines. Reactions of the title compound with less basic aromatic amines (aniline, p-anisidine, and p-phenetidine) involve both nitrovinyl groups of the dinitrodiene, leading to 1,1,3-tris(arylamino)-4-chloro-2,4-dinitro-1,3-butadienes. Treatment of tetrachloro-1,3-dinitro-1,3-butadiene with phenylmethanethiol gave 1-benzylthio-1,3,4-trichloro-2,4-dinitro-1,3-butadiene which reacted with piperidine to form product of chlorine replacement only in the α-nitrovinyl group; the reaction of 1-benzylthio-1,3,4-trichloro-2,4-dinitro-1,3-butadiene with aniline occurred at both nitrovinyl moieties. By reactions of tetrachloro-1,3-dinitro-1,3-butadiene with difunctional nucleophiles the corresponding 2-(2,3-dichloro-1,3-dinitro-2-propenylidene)-substituted heterocyclic compounds were obtained.