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Published on: April 26, 2024
Nitrolysis of a Highly Deactivated Amide by Protonitronium. Synthesis and Structure of HNFX(1)
Robert D. Chapman1, Richard D. Gilardi, Mark F. Welker
1Naval 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.
Abstract:
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).
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