Nitrolysis of a Highly Deactivated Amide by Protonitronium. Synthesis and Structure of HNFX(1).
Efficient N-nitrolysis of highly deactivated 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-bis(4-nitrobenzenesulfonyl)-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).
Chapman
Robert D.
RD
Naval Aviation Science & Technology Office (Code 4T4220D), Naval Air Warfare Center Weapons Division, China Lake, California 93555, Laboratory for the Structure of Matter (Code 6030), Naval Research Laboratory, 4555 Overlook Avenue SW, Washington, D.C. 20375, and TPL, Inc., 3921 Academy Parkway North NE, Albuquerque, New Mexico 87109.
Gilardi
Richard D.
RD
Welker
Mark F.
MF
Kreutzberger
Charles B.
CB