N-DENITRATION OF NITRAMINES BY DIHYDRONICOTINAMIDES

摘要

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 nitramines 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 deniaohydrogenation mechanism is achieved either by photolysis or chemically by dithionite ion. A polymer-supported analogue of BNAH effects similar, though slower, N-denitration. Copyright (C) 1996 Elsevier Science Ltd. [References: 36]