Benzylamine-free, heavy-metal-free synthesis of CL-20 via hexa(1-propenyl)hexaazaisowurtzitane

Journal of Energetic Materials

Volumn 26, Issue 4, 2008, Pages 246-273

  Chapman, Robert D ^a   Hollins, Richard A ^a  

^a NAVAL AIR WARFARE CENTER   (United States)

Author keywords

CL 20; Hexa (1 propenyl)hexa azaisowurtzitane; Hexa allylhexaazaisowurtzitane; Hexa nitrohexa azaisowurtzitane; Polyformylhexa azaisowurtzitane

Indexed keywords

EID: 49449091280     PISSN: 07370652     EISSN: 15458822     Source Type: Journal    
DOI: 10.1080/07370650802182385     Document Type: Article

References (42)

1. (a) Nair, U. R., R. Sivabalan, G. M. Gore, M. Geetha, S. N. Asthana, and H. Singh. 2005. Hexanitrohexaazaisowurtzitane (CL-20) and CL-20-based formulations (Review). Combustion, Explosion and Shock Waves, 41: 121;
2. (b) Sysolyatin, S. V., A. A. Lobanova, Yu. T. Chernikova, and G. V. Sakovich. 2005. Methods of synthesis and properties of hexanitrohexaazaisowurtzitane. Russian Chemical Reviews, 74: 757.
3. Schulz, W. The Many Faces of Chlorine. 2004. Available at: http://pubs.acs.org/cen/ncw2004/8242chlorine.html (accessed 26 June 2008).
4. The Global Chlorine Crisis. 1996. Available at: http://archive.greenpeace.org/toxics/reports/cfap/cfapm2.html (accessed 26 June 2008).
5. Mercury Process for Making Chlorine. 1998. Available at: http://www.eurochlor.org/upload/documents/document109.pdf (accessed 26 June 2008).
6. 3,11]dodecanes from glyoxal and benzylamines. Journal of Organic Chemistry, 55: 1459.
7. Lower Cost, Improved Quality CL-20 Energetic Material. 2002. Available at: https://www.dodmantech.com/successes/Navy/weapons/ weapons _LowerCostCL20_120805.pdf (accessed 26 June 2008). [7] (a) Wardle, R. B. and J. C. Hinshaw. 2000. Method for making new polycyclic polyamides as precursors for energetic polycyclic polynitramine oxidizers. U.S. Patent 6,147,209;
8. (b) Wardle, R. B. and J. C. Hinshaw. 2006. Polycyclic, polyamides as precursors for energetic polycyclic polynitramine oxidizers. U.S. Patent 7,129,348.
9. Hervé, G., G. Jacob, and R. Gallo. 2006. Preparation and structure of novel hexaazaisowurtzitane cages. Chemistry - A European Journal, 12: 3339.
10. Cagnon, G., G. Eck, G. Hervé, and G. Jacob. 2007. Process for the 2-stage synthesis of hexanitrohexaazaisowurtzitane starting from a primary amine. U.S. Patent 7,279,572.
11. Foote, C. S. and J. W.-P. Lin. 1968. Chemistry of singlet oxygen. VI. Photooxygenation of enamines: Evidence for an intermediate. Tetrahedron Letters, 9: 3267.
12. Price, C. C. and W. H. Snyder. 1962. The base-catalyzed isomerization of allyl to propenyl amines. Tetrahedron Letters, 3: 69.
13. HPIW here must be distinguished from hexapiperonylhexaazaisowurtzitane previously reported: Tsai, H.-J., C.-M. Ho, T.-H. Ting, M.-J. Liu, J.-S. Lee, and L.-C. Shu. 2003. Synthesis of HNIW high energetic cage compound. Hua Hsueh (Taipei), 61: 199.
14. (a) Sauer, J. and H. Prahl. 1966. Isomerisierungen von N,N-Dialkylallylaminen mit Basen zu cis-Enaminen. Tetrahedron Letters, 7: 2863;
15. (b) Carlsen, P. H. J. and K. B. Jørgensen, 1997. Thermolysis of N-allylic 1,2,4-triazoles. Journal of Heterocyclic Chemistry, 34: 797.
16. Gottlieb, H. E., V. Kotlyar, and A. Nudelman. 1997. NMR chemical shifts of common laboratory solvents as trace impurities. Journal of Organic Chemistry, 62: 7512.
17. Kölle, U., B. Kolb, and A. Mannschreck. 1980. Konformation und Stereodynamik dipolarer cyclischer Enamine und Hydrazone. Chemische Berichte, 113: 2545.
18. Foote, C. S. and A. A. Dzakpasu. 1975. Chemistry of singlet oxygen. XX. Mechanism of the sensitized photooxidation of enamines. Tetrahedron Letters, 16: 1247.
19. 2O). Youji Huaxue, 25: 1259.
20. Martin, N. H. and C. W. Jefford. 1982. Synthesis and photooxygenation of some substituted l-benzyl-3,4-dihydroisoquinolines. Mechanism of enamine photooxygenation. Helvetica Chimica Acta, 65: 762.
21. Cook, A. G. 1988. Enamines: Synthesis, Structure, and Reactions. 2nd ed. New York: Marcel Dekker.
22. 3,11]dodecane (HBIW). Perkin Transactions 2, 1993: 923.
23. 6). International Annual Conference of ICT [Proceedings], Karlsruhe, Germany, June 27-30, 31 (Energetic Materials): 109=1-109=14.
24. Martin, N. H. and C. W. Jefford. 1981. Evidence for a charge-transfer mechanism in the photo-oxygenation of an enamine. Tetrahedron Letters, 22: 3949.
25. Baranova, N. M., A. D. Yakusheva, and P. N. Komarov. 1978. Dimeric isosafrole peroxide and its thermal decomposition. Journal of Organic Chemistry USSR, 14: 2210.
26. Kim, H.-S., K. Begum, N. Ogura, Y. Wataya, Y. Nonami, T. Ito, A. Masuyama, M. Nojima, and K. J. McCullough. 2003. Antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes and 1,2,5-trioxacycloalkanes. Journal of Medicinal Chemistry, 46: 1957.
27. Jefford, C. W., J.-C. Rossier, S. Kohmoto, and J. Boukouvalas. 1985. Acid-catalyzed cleavage of 1,4-dimethyl-l,4-dihydronaphthalene 1,4-endoperoxide. Reactivity of the resulting hydroperoxy carbocation with nucleophiles. Helvetica Chimica Acta, 68: 1804.
28. Dunning, T. and W. J. Dunning. 1950. Methylene-nitramines. Part I. The reaction of hexamine dinitrate with nitric acid at low temperatures. Journal of the Chemical Society, 1950: 2920.
29. Bonner, T. G., R. A. Hancock, and J. C. Roberts. 1972. The N-nitroxymethyl derivatives of 1,3-dinitroperhydro-1,3,5-triazine, piperidine, and succinimide. Perkin Transactions 1, 1972: 1902.
30. Ando, W., T. Saiki, and T. Migita. 1975. Singlet oxygen reaction. IV. Photooxygenation of enamines involving a two-step cleavage of a 1,2-dioxetane intermediate. Journal of the American Chemical Society, 97: 5028.
31. 1H-NMR, Raman and I.R. spectroscopy. Spectrochimica Acta, 39A: 569.
32. Nemet, I., D. Vikić-Topić, and L. Varga- Defterdarović. 2004. Spectroscopic studies of methylglyoxal in water and dimethylsulfoxide. Bioorganic Chemistry, 32: 560.
33. Zioudrou, C., C. I. Stassinopoulou, and S. Loukas. 1980. On the mechanism of isomerization of a-hydroxypropionaldehyde to hydroxyacetone. Bioorganic Chemistry, 9: 163.
34. Hickmott, P. W. 1994. Electrophilic and nucleophilic substitution and addition reactions of enamines. In Z. Rappaport (ed.), The Chemistry of Enamines, New York: John Wiley.
35. Kamm, O. and C. S. Marvel. 1941. Allyl alcohol. Organic Syntheses Collective Volume I, 42.
36. Norris, J. F., M. Watt, and R. Thomas. 1916. The reaction between alcohols and aqueous solutions of hydrochloric and hydrobromic acids. Journal of the American Chemical Society, 38: 1071.
37. McCullough, R. and F. Cortese. 1929. The action of sulfuric acid in the preparation of certain alkyl halides. Journal of the American Chemical Society, 51: 225.
38. Peters, L. M., K. E. Marple, T. W. Evans, S. H. McAllister, and R. C. Castner. 1948. Methacrylonitrile and acrylonitrile: Production by oxidation of methallyl- and allylamine. Industrial and Engineering Chemistry, 40: 2046.
39. Li, X.-L., C.-H. Sun, X.-Q. Zhao, and J.-W. Song. 2007. Synthesis of hexaallylhexaazaisowurtzitane. Hanneng Cailiao, 15: 490.
40. Nielsen, A. T. and R. A. Nissan. 1986. Polynitropolyaza Caged Explosives Part 5 (TP 6692). China Lake, CA: Naval Weapons Center.
41. Nielsen, A. T. 1986. Synthesis of polycyclic nitramine explosives. American Defense Preparedness Association Symposium on Compatibility of Plastics and Other Materials with Explosives, Propellants, Pyrotechnics & Processing of Explosives, Propellants and Ingredients [Proceedings], Long Beach, CA, October 28, p. 118-121.
42. Christe, K. O. and A. J. Alfano. 2003. Process for the chemical generation of singlet delta oxygen. U.S. Patent 6,623,718.