Nitrolysis of a highly deactivated amide by protonitronium. Synthesis and structure of HNFX

Efficient N-nitrolysis of highly deactivated 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-bis(4-ni- trobenzenesulfonyl)-1,5-diazocine (1) has been achieved by the use of protonitronium reagent formed in the system nitric acid-trifluoromethanesulfonic acid, producing 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-dinitro-1,5-diazocine (HNFX, 2) in 65% yield in a nonoptimized reaction. The crystal structure of the first morphology of HNFX contains cavities in the form of channels through its unit cell; the observed density is 1.807 g . cm(-3).