Patent ID: 7632943

Claim:
A method for making 3,3,7,7-tetrakis-(difluoramino)octahydro-1,5-dinitro-1,5-diazocine (HNFX) comprising: providing an effective amount of a suitably N-protected tetrahydro-1,5-disulfonyl-1,5-diazocine-3,7(2H,6H)-dione (A); subjecting said dione to difluoramination to produce a 3,3,7,7 tetrakis(difluoramino)octahydro-1,5-disulfonyl-1,5-diazocine intermediate (B), wherein said R on said 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-disulfonyl-1,5-diazocine intermediate (B) comprises at least one of halo, polyhaloalkyl, polyhaloaryl, a regioisomer of cyanoaryl, polycyanoaryl, a regioisomer of nitroaryl, polynitroaryl, and heteroaryl; subjecting an effective amount of said 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-disulfonyl-1,5-diazocine intermediate (B) to protolytic N-deprotection in a nitrating species free reaction by adding an acid with a Hammett acidity constant (H 0 ) less than that of sulfuric acid (approximately −11) to form a salt of deprotected 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-diazocinium intermediate cation (C); and subjecting said salt of intermediate salt (C) to nitration utilizing an electrophilic nitrating agent to form 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-dinitro-1,5-diazocine (HNFX) having the formula