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Synthesis of High Density Insensitive Energetic Tetraazapentalene Derivatives

Published online by Cambridge University Press:  10 February 2011

M. L. Trudell ,
G. Subramanian ,
G. Eck  and
J. H. Boyer
M. L. Trudell
Affiliation:
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, [email protected]
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Abstract

An improved nitration procedure has been developed for the synthesis of y-Tacot (3). The synthesis of y-DBBD (8) has been completed in three steps from 3 in 37% yield. y-DBBD (8) was found to be thermally stable up to 274 °C (decomposed) and insensitive to impact (hammer blow). Nitration of z-BDDB (6) and y-DBBD (8) gave carbonyl derivatives resulting from in situ hydroysis/oxidation of the corresponding tetranitro derivatives z-TBBD (7) and y-TBBD (9), respectively.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 418: Symposium GG – Decomposition, Combustion, and Detonation Chemistry of Energetic Materials , 1995 , 37
Copyright
Copyright © Materials Research Society 1996

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References

1. Urbanski, T. and Vasudeva, S.K., J. Scient. Ind. Res. 37, 250 (1978).Google Scholar
2. Carboni, R.A., Kauer, J.C., Hatchard, W.R. and Harder, R.J., J. Am. Chem. Soc. 89, 2626 (1967).Google Scholar
3. Carboni, R.A., U.S. Patent No. 2 904 545 (1959).Google Scholar
4. Kauer, J.C. and Carboni, R.A., J. Am. Chem. Soc. 89, 2633 (1967).Google Scholar
5. Kauer, J.C., U.S. Patent No. 3 262 943 (26 July 1966).Google Scholar
6. Berlin, J.K. and Coburn, M.D., J. Heterocycl. Chem. 12, 235 (1975).Google Scholar
7. Wartenberg, C., Charrue, P. and Lavel, F., Prop. Expl. Pyro. 20, 23 (1995).Google Scholar
8. Nielsen, A.T., in Chemistry of Energetic Materials, edited by Olah, G. and Squire, D.R. (Academic Press Inc., New York, 1991), pp. 95–124.Google Scholar
9. Meyer, R., Explosives, 3rd ed. (VCH, Weinheim, 1987), p. 150 and 202. (RDX; mp 204 °C; d = 1.81 g/cm3; D = 8.85 mm/sec) (HMX; mp 282 °C; d = 1.9 g/cm3; D = 9.1 mm/sec)Google Scholar
10. The density d (g/cm3), detonation velocity D (mm/sec) and detonation pressure P CJ (kbar) were computed with a program obtained from the Naval Weapons Center, China Lake, CA.Google Scholar
11. Subramanian, G., Boyer, J.H., Buzatu, D., Stevens, E.D., and Trudell, M.L., J. Org. Chem. 60, 6110 (1995).Google Scholar
12. Koppes, W., Naval Surface Warfare Center, Indian Head, MD 20640–5035 (private communication).Google Scholar
13. Stevens, E.D., University of New Orleans (private communication).Google Scholar
14. Biffin, M.E., Miller, J., and Paul, D.B., in The Chemistry of the Azido Group, edited by Patai, S. (Wiley and Sons, New York 1971), pp. 209–212.Google Scholar
15. Olah, G.A., Malhorta, R. and Narang, S.C., Nitration, (VHC Publishers Inc., New York, 1976), pp. 9–83.Google Scholar
16. Subramanian, G., Boyer, J.H., Koppes, W., Gilardi, R., and Trudell, M.L., J. Org. Chem. (submitted).Google Scholar
17. Urbanski, T., Chemistry and Technology of Explosives, (Pergamon Press, Oxford, 1964), pp 258–259.Google Scholar