SYNTHESIS OF POLYNITRO COMPOUNDS - HEXASUBSTITUTED BENZENES
SYNTHESIS OF POLYNITRO COMPOUNDS - HEXASUBSTITUTED BENZENES
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DOI：
10.1021/jo00367a003
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发表时间：
1986-08-22
影响因子：
3.6
通讯作者：
WILSON, WS
中科院分区：
文献类型：
--
作者：
ATKINS, RL;HOLLINS, RA;WILSON, WS
本文介绍了由一种合适的氨基二硝基甲苯硝化合成三种异构的氨基四硝基甲苯，并讨论了4-氨基-2，6-二硝基甲苯表观自硝化生成五硝基苯胺的反应。本文叙述了异构体氨基四硝基甲苯氧化成五硝基甲苯，以及五硝基苯胺和五硝基甲苯的氨解反应。我们对具有炸药和推进剂用途的高能材料高度硝化物的持续兴趣，促使我们研究制备全硝化芳族体系的方法。2-5 2，4，6-三硝基甲苯（TNT，1）的多硝基芳族类似物和多氨基多硝基芳族化合物有望在密度、功率、灵敏度和稳定性等方面表现出更好的性能，但这些化合物的合成很少。本文研究了异构体2-氨基-3，4，5，6-，3-氨基-2，4，5，6-和4-氨基-2，3，5，6-四硝基甲苯（2，3，4）的合成、反应及其氧化成2，3，4，5，6-五硝基甲苯（5）。本文还讨论了4-五硝基苯胺（6）的表观自硝化反应，并由此制得六硝基苯（7）和1，3，5-三氨基-2，4，6-三硝基苯（TATB，8）。
The synthesis of the three isomeric aminotetranitrotoluenes by nitration of an appropriate aminodinitrotoluene is presented, and the apparent ipso nitration of 4-amino-2, 6-dinitrotoluene to give pentanitroaniline is also discussed. The oxidation of the isomeric aminotetranitrotoluenes to pentanitrotoluene is described, as is the ammonolysis of pentanitroaniline and of pentanitrotoluene.Our continuing interest in highly nitrated species, en-ergetic materials which have explosive and propellant applications, has prompted us to investigate methods of preparation of pernitrated aromatic systems. 2-5 Polynitroaromatic analogues of 2, 4, 6-trinitrotoluene (TNT, 1) and polyaminopolynitroaromatic compounds are expected to show improved propertiesof density, power, sensitivity and stability, but few of these species have been synthesized. This study deals, then, with the synthesis and reactions of the isomeric 2-amino-3, 4, 5, 6-, 3-amino-2, 4, 5, 6-, and 4-amino-2, 3, 5, 6-tetranitrotoluenes (2, 3, and 4) and their oxidation to 2, 3, 4, 5, 6-pentanitrotoluene (5). We also discuss theapparent ipso nitration of 4 to 2, 3, 4, 5, 6-pentanitroaniline (6) from which hexanitrobenzene (7) and 1, 3, 5-triamino-2, 4, 6-trinitrobenzene (TATB, 8) may be prepared.