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 achi eved by the use of protonitronium reagent formed in the system nitric acid- trifluoromethanesulfonic acid, producing 3,3,7,7-tetrakis(difluoramino)octa hydro-1,5-dinitro-1,5-diazocine (HNFX, 2) in 65% yield in a nonoptimized re action. The crystal structure of the first morphology of HNFX contains cavi ties in the form of channels through its unit cell; the observed density is 1.807 g . cm(-3).