Synthesis and reactions of 1,1-diamino-2,2-dinitroethylene

Article abstract of DOI:10.1016/S0040-4020(98)00673-5

Low temperature nitrations of 2-methylimidazole gave in addition to the known 2-methyl-5(4)-nitroimidazole (1), 2- (dinitromethylene)-5,5-dinitro-4- imidazolidinone (3) and parabanic acid (2). The tetranitro compound 3 was also obtained by nitration of 2-methyl-4,5-dihydro-(1H)-5-imidazolone (8). Thermal decomposition of 3 gave 2-(dinitromethylene)-4,5-imidazolidinedione (4) which also was the product from nitration of the new compound 2-methoxy- 2-methyl-4,5- imidazolidinedione. Treatment of 4 with aqueous ammonia gave the previously unknown 1,1-diamino-2,2-dinitroethylene (5). The physical properties and chemical behaviour of (5) are described.