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
- Authors: Kalashnikov A.I.1, Sysolyatin S.V.1,2, Sakovich G.V.1, Dubkov A.S.1, Kulagina D.A.1
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Affiliations:
- Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences
- National Research Tomsk State University
- Issue: Vol 66, No 3 (2017)
- Pages: 531-536
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/240264
- DOI: https://doi.org/10.1007/s11172-017-1767-y
- ID: 240264
Cite item
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.
About the authors
A. I. Kalashnikov
Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences
Author for correspondence.
Email: admin@ipcet.ru
Russian Federation, 1 ul. Sotsialisticheskaya, Altai Krai, Biysk, 659322
S. V. Sysolyatin
Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences; National Research Tomsk State University
Email: admin@ipcet.ru
Russian Federation, 1 ul. Sotsialisticheskaya, Altai Krai, Biysk, 659322; 36 prosp. Lenina, Tomsk, 634050
G. V. Sakovich
Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences
Email: admin@ipcet.ru
Russian Federation, 1 ul. Sotsialisticheskaya, Altai Krai, Biysk, 659322
A. S. Dubkov
Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences
Email: admin@ipcet.ru
Russian Federation, 1 ul. Sotsialisticheskaya, Altai Krai, Biysk, 659322
D. A. Kulagina
Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences
Email: admin@ipcet.ru
Russian Federation, 1 ul. Sotsialisticheskaya, Altai Krai, Biysk, 659322