Hydroxynitrobenzodifuroxan and its salts

Journal of Heterocyclic Chemistry

Volumn 42, Issue 6, 2005, Pages 1117-1125

  Sitzmann, Michael E ^a   Bichay, Magdy ^a   Fronabarger, John W ^b   Williams, Michael D ^b   Sanborn, William B ^b   Gilardi, Richard ^c  

^a NAVAL SURFACE WARFARE CENTER   (United States)

^b Pacific Scientific Energetic Materials Co   (United States)

^c NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CESIUM; EXPLOSIVE; HYDROXYNITROBENZODIFUROXAN; METAL; NITROGEN; POTASSIUM SALT; PYRROLE DERIVATIVE; RUBIDIUM; SODIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ISOMER; MATERIALS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 24944484201     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570420613     Document Type: Article

References (14)

1. R. J. Spear and W. P. Norris, Propellants, Explosives, Pyrotechnics, 8, 85 (1983).
2. W. P. Norris, A. Chafin, R. J. Spear and R. W. Read, Heterocycles, 22, 8 (1984).
3. By J. W. Fronabarger. In U. S. Patent application: John W. Fronabarger and Michael E. Sitzmann, "Nitrobenzodifuroxan Compounds, Including Their Salts, and Methods Thereof", 13 Aug 2003.
4. P. N. Preston and G. Tennant, Chem. Rev., 72, 650 (1972).
5. Our initial attempt to prepare such a hydrolyzable intermediate (namely, 3,5-diazido-2,4,6-trinitrochlorobenzene), by treating 1,3,5-trichloro-2,4,6- trinitrobenzene with two equivalents of sodium azide was unsuccessful, the idea being to replace two of the chloro groups with azide and use the remaining chloro group as the hydrolysable moiety. The reaction furnished instead primarily a mixture of starting material and 1,3,5-triazido-2,4,6- trinitrobenzene. Thus, it would appear that azide replacement of chloride in trichlorotrinitrobenzene activates the remaining chloro groups toward further displacement by azide, thereby favoring formation of the triazido compound.
6. D. G. Ott and T. M. Benziger, U. S. Patent 4,952,733 (1990); Chem. Abstr., 114, 142852a (1991).
7. 6 nmr solvents were sufficient to cause some hydrolysis of 4 and generate a peak for methanol (see Experimental Section).
8. A. J. Boulton and A. R. Katritzky, Proc. Chem. Soc., London, 257 (1962).
9. A. J. Boulton, A. C. Gripper-Grey, and A. R. Katritzky, J. Chem. Soc., 5958 (1965).
10. Dihydrazinotetrazine is available via a simplified method recently reported. See D. E. Chavez and M. A. Hiskey, J. Heterocyclic Chem., 35, 1329 (1998).
11. Form B and form A would be expected to produce 4 and 6 peaks, respectively.
12. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications CCDC-256738 for the potassium salt of 1, CCDC-256737 for the rubidium salt, and CCDC-256736 for the guanidinium salt. Copies of the data can be obtained freely on application to CCDC, 12 Union Road, Cambridge CB2 1EZ (UK); Tel.: (+44) 1223-336-408, Fax: (+44) 1223-336-033, and E-mail: deposit@ccdc.cam.ac.uk
13. For the preparation of the solution containing purified 1, see general experimental section.
14. -1.