N-denitration of nitramines by dihydronicotinamides

Article abstract of DOI:10.1016/0040-4020(96)00502-9

N-NO₂ bond scission in organic nitramines occurs in high yields by reaction with 1,4-dihydronicotinamides. HMX (3) and tetryl (4) were used as model aliphatic and aromatic nitremines in reactions with 1-benzyl-1,4- dihydronicotinamide (BNAH, 1), resulting in hexamethylenetetramine and N- methylpicramide (5), respectively, as the predominant products. Radical initiation of the electron-transfer denitrohydrogenation mechanism is achieved either by photolysis or chemically by dithionite ion. A polymer- supported analogue of BNAH effects similar, though slower, N-denitration.