Abstract
The synthetic methodology which has been utilized to prepare a number of polynitropolycyclic cage explosives in our laboratory is presented, and the underlying strategy is described in each case. The results of thermodynamic studies of several polynitropolycyclic systems are presented and discussed along with preliminary results of explosive. evaluation studies which have been performed on D3-hexanitrotrishomocubane and on 4,4,8,8,11,11-hexanitropentacyclo[5.4.0.02,6.03,10.05,9]undecane.
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References
Campbell, C. (1987) U. S. Army Armament Research, Development and Engineering Center, Picatinny Arsenal, NJ, Personal communication.
Campbell, C. (1991) U. S. Army Armament Research, Development and Engineering Center, Picatinny Arsenal, NJ, Personal communication.
Dave, P. R., Ferraro, M., Ammon, H. L., and Choi, C. S. (1990), ‘Synthesis of 2,2,4,4-Tetranitroadamantane’, J. Org. Chem., 54, 4459–4461.
Eaton, P. E., Shankar, B. K. R., Price, G. D., Pluth, J. J., Gilbert, E. E., Alster, J., and Sandus, O. (1984) ‘Synthesis of 1,4-Dinitrocubane’,J. Org. Chem., 49, 185–186.
Hamlin, K. E. and Weston, A. W. (1957) ‘The Cleavage of Non-Enolizable Ketones with Sodium Amide. The Haller-Bauer Reaction’, Org. React., 9, 1–36.
Jayasuriya, K. (1990) GEO-CENTERS, Inc., Lake Hopatcong, NJ, Personal communcation.
Klimova, T. A., Krayushkin, M. M., Sevost’yanova, V. V., and Novikov, S. S. (1974) ‘Synthesis of 3,7-Dinitronoradamantane’, Izv. Akad. Nauk SSR, Ser. Khim., p. 26–56.
Kornblum, N., Singh, H. K., and Kelly, W. J. (1983) ‘Oxidative Substitution of Nitroparaffin Salts’, J. Org. Chem., 48, 332–337.
Marchand, A. P. and Suri, S. C. (1984) ‘Synthesis of 3,5,5-Trinitropentacyclo[5.3.0.02,6.03,10,04’8ldecane’, J. Org. Chem., 49, 2042–2043.
Marchand, A. P., Jin, P.-w., Flippen-Anderson, J. L., Gilardi, R., and George, C. ‘A Novel Rearrangement in a 1,3-Bishomocubyl Ring System’, J. Chem. Soc., Chem. Commun., pp. 1108–1109.
Marchand, A. P., Sharma, G. V. M., Annapurna, G. S., and Pednekar, P. R. (1987) ‘Pentacyclo[6.3.0.02,6,03,10,05,9lundecane-4,7,11-trione (D3-Trishomocubanetrione), and 4,4,7,7,11,11-Hexanitro[6.3.0.02,6.03,10.05,9]undecane ( D3-Hexanitrotrishomocubane)’, J. Org. Chem., 52, 4784–4788.
Marchand, A. P. (1988) ‘Synthesis and Chemistry of Novel Polynitropolycyclic Cage Molecules’, Tetrahedron, 44, 2377–2395.
Marchand, A. P., Arney, B. E., Jr., and Dave, P. R. (1988) ‘Synthesis of 8,8,11,11-Tetranitropentacyclo[5.4.0.02,6 03,10.05,9lundecane’, J. Org. Chem., 53, 443–446.
Marchand, A. P., Dave, P. R., Rajapaksa, D., Arney, B. E., Jr., Flippen-Anderson, J. L., Gilardi, R., and George, C. (1989), ‘Synthesis of 4,4,8,8,11,11-Hexanitropentacyclo[5.4.0.02,6 03,10.05,9]_undecane’, J. Org. Chem., 54, 1769–1771.
Marchand, A. P., Sharma, R., Zope, U. R., Watson, W. H., and Kashyap, R. P. (1992), ‘Syntheses of 2,2,5,5-Tetranitronorbornane and 2,2,7,7-Tetranitronorbornane’, J. Org. Chem., Manuscript submitted.
Murray, R. W., Rajadhyaksha, S. N., and Mohan, L. (1989) ‘Oxidation of Primary Amines by Dimethyldioxirane’, J. Org. Chem., 54, 5783–5788.
Nielsen, A. T. (1962) ‘The Isomeric Dinitrocyclohexanes. I. Synthesis of Epimeric 1,3- and 1,4-Dinitrocyclohexanes’, J. Org. Chem., 27, 1993–1998.
Olah, G. A., Ramaiah, P., Surya Prakash, G. K., and Gilardi, R. (1992), `Polynitronorbornanes, Bicyclooctanes, and Cyclohexanes’, J. Org. Chem., Manuscript submitted.
Paquette, L. A., Fischer, J. W., and Engel, P. (1985) ‘Synthesis and X-ray Crystal Structure Analysis of a Vicinally Dinitro-Substituted Bishomopentaprismane’ J. Org. Chem., 50, 2524–2527.
Sandus, O. (1985). U. S. Army Armament Research, Development, and Engineering Center, Picatinny Arsenal, NJ, Personal communication.
Shiori, T., Ninomiya, K., and Yamada, S.-I. (1972) ‘Diphenylphosphoryl Azide. A New Convenient Reagent for a Modified Curtius Reaction and for the Peptide Synthesis’, J. Am. Chem. Soc., 94, 6203–6205.
Velicky, R. W. (1986) ‘An Explosive Output Laboratory Test Employing the Slapper Technique to Stimulate Detonations’, Technical Report No. ARAED-TR-86036, ARDC, Dover, NJ, October, 1986.
Velicky, R. W., Iyer, S., Campbell, C., Sandus, O., Alster, J., Marchand, A. P., Sharma, G. V. M., and Annapurna, G. S. (1988), ‘Thermal Behavior and Detonation Properties of D3 -Hex anitrotrishomocubane’, J. Energetic Materials, 6, 145–152.
Walters, T. R., Zajac, W. W., Jr., and Woods, J. M. (1991) ‘New Reagents for the Synthesis of gem-Halonitro Compounds from Oximes’, J. Org. Chem., 56, 316–321.
Weinstein, D. I., Alster, J., and Marchand, A. P. (1986) ‘Thermal Studies of Polynitrobishomocubanes’, Thermochimica Acta, 99, 133–137
Zajac, W. W., Jr., Walters, T. R., and Woods, J. M. (1989) ‘1-Amino3,5,7-trinitroadamantane: An Unexpected Oxidation Product of 1,3,5,7-Tetraaminoadamantane. An Improved Synthesis of 1,3,5,7Tetranitroadamantane’, J. Org. Chem., 54, 2468–2471.
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© 1993 Springer Science+Business Media Dordrecht
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Marchand, A.P. et al. (1993). Synthesis and Explosive Performance Characteristics of Polynitropolycyclic Cage Explosives. In: Yinon, J. (eds) Advances in Analysis and Detection of Explosives. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-0639-1_24
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DOI: https://doi.org/10.1007/978-94-017-0639-1_24
Publisher Name: Springer, Dordrecht
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