Advertisement

Russian Chemical Bulletin

, Volume 66, Issue 3, pp 531–536 | Cite as

Nitrolysis of 2,6,8,12-tetraacetyl-4,10-dibenzyl-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane

  • A. I. Kalashnikov
  • S. V. Sysolyatin
  • G. V. Sakovich
  • A. S. Dubkov
  • D. A. Kulagina
Full Articles

Abstract

Nitrolysis of 2,6,8,12-tetraacetyl-4,10-dibenzyl-2,4,6,8,10,12-hexaazatetracyclo-[5.5.0.03,11.05,9]dodecane results in the substitution of benzyl groups by the nitro groups with the formation of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]-dodecane. The reaction sequentially proceeds through the nitration of the benzyl groups predominantly at para-position, the substitution of one nitrobenzyl group with the nitro group, and the introduction of the second nitro group into the nitrobenzyl fragment. The replacement of the remaining dinitrobenzyl fragment is a more difficult process, which reaches completion only by the end of the nitration. Another reaction product is p-nitrobenzoic acid, which is formed in the secondary reactions. No substitution of a p-nitrobenzoyl group with the nitro group takes place in the nitration of 2,6,8,12-tetraacetyl-4,10-di(p-nitrobenzoyl)-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane under similar conditions.

Key words

2,6,8,12-tetraacetyl-4,10-dibenzyl-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]-dodecane nitrolysis N-nitro compounds 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    S. V. Sysolyatin, A. A. Lobanova, Yu. T. Chernikova, G. V. Sakovich, Russ. Chem. Rev., 2005, 8, 757.CrossRefGoogle Scholar
  2. 2.
    A. T. Nielsen, A. P. Chafin, S. L. Christian, D. W. More, M. P. Nadler, R.A. Nissan, D. J. Vanderah, Tetrahedron, 1998, 54, 11793.CrossRefGoogle Scholar
  3. 3.
    US Pat. 5739325; Chem. Abstrs., 1998, 127, 110983.Google Scholar
  4. 4.
    S. V. Sysolyatin, V. V. Malykhin, Russ. Chem. Rev., 2014, 83, 949.Google Scholar
  5. 5.
    PCT Int. Appl. WO 9623792; Chem. Abstrs., 1998, 125, 275920.Google Scholar
  6. 6.
    A. I. Kalashnikov, S. V. Sysolyatin, G. V. Sakovich, I. A. Surmacheva, V. N. Surmachev, Yu. T. Lapina, Russ. Chem. Bull., 2009, 58, 2164.CrossRefGoogle Scholar
  7. 7.
    N. V. Latypow, U. Wellmar, P. Goed, A. J. Bellamy, Organic Process Research & Development, 2000, 4, 156.CrossRefGoogle Scholar
  8. 8.
    S. V. Sysolyatin, G. V. Sakovich, A. I. Kalashnikov, Y. T. Chernikova, V. N. Surmachev, A. A. Lobanova, 38st Int. Ann. Conf. of ICT Energetic Materials. Characterisation and Performance of Advanced Systems (Karlsruhe, FRG, June 27–29, 2007), Fraunhofer ICT, 2007, P 47.Google Scholar
  9. 9.
    G. Jacob, G. Lacroix, V. Destombes, 31st Int. Ann. Conf. of ICT Energetic Materials: Analizys, Diagnostic and Testing (Karlsruhe, FRG, June 27–30, 2000), Fraunhofer ICT, 2000, P 106.Google Scholar
  10. 10.
    P. Maksimowski, M. Duda, W. Tomaszewski, Propellants Explos. Pyrotech., 2011, 36, 320.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • A. I. Kalashnikov
    • 1
  • S. V. Sysolyatin
    • 1
    • 2
  • G. V. Sakovich
    • 1
  • A. S. Dubkov
    • 1
  • D. A. Kulagina
    • 1
  1. 1.Institute for Problems of Chemical and Energetic TechnologiesSiberian Branch of the Russian Academy of SciencesAltai Krai, BiyskRussian Federation
  2. 2.National Research Tomsk State UniversityTomskRussian Federation

Personalised recommendations