• Applied Chemistry for Engineering
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• v.25 no.2
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• pp.188-192
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• 2014

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.