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http://dx.doi.org/10.14478/ace.2014.1005

Nitration of 3,7,9,11-Tetraoxo-2,4,6,8,10-pentaaza[3.3.3]propellane  

Shin, Moonyong (Department of Chemical and Biological Engineering, Seoul National University)
Ha, Tae-Hwan (Department of Chemical and Biological Engineering, Seoul National University)
Chung, Kyoo-Hyun (Department of Chemistry, Inha University)
Kim, Jin Seuk (Agency for Defense Development)
Kim, Young Gyu (Department of Chemical and Biological Engineering, Seoul National University)
Publication Information
Applied Chemistry for Engineering / v.25, no.2, 2014 , pp. 188-192 More about this Journal
Abstract
Until now, there has been much efforts for the development of polycyclic molecules as high energy materials because of their high density and potential energy. However, there were only a few reports on the development of highly N-substituted polycyclic compounds due to difficulties of the synthesis. We have designed pentaazapropellanes as new high energy materials and we have recently reported unsubstituted 3,7,9,11-tetraoxo-2,4,6,8,10-pentaaza[3.3.3]propellane (TOPAP) 2 as a new skeleton for high energy materials. Herein, the nitration of TOPAP 2 was reported for the first time. Thus, 2,6-dinitro-3,7,9,11-ttraoxo-2,4,6,8,10-pentaaza[3.3.3]propellane (2,6-DNTOPAP) 5C, which is a new nitro derivative of TOPAP 2, was obtained up to 82% yield by the reaction of $NO_2BF_4$ and anhydrous $HNO_3$. The structure of 5C was determined by spectroscopic analysis.
Keywords
High energy materials; pentaazapropellane; nitroazapropellane;
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