Reactions of Benzotriazolo[2,1-a]benzotriazole Derivatives. 1. Synthesis of New Insensitive High-Density Energetic Compounds

Abstract

Abstract : The sequential preference of electrophilic attack on the dibenzotetraazapentalene ring system 6 has unequivocally been shown to be in the order of position 2(8) > 4(10) >> 1(7) and 3(9). However, nucleophilic substitution reactions with sodium azide were found to be substrate dependent. Substitution occurred at the 3(9)-position of 9 followed by elimination of hydrogen chloride to give 10 while direct substitution of azide for the 4(10)-nitro group of 2 was found to yield 13. The reactivity of the dibenzotetraazapentalene derivatives toward electrophiles and nucleophiles was exploited for the synthesis of the new heterocyclic system 3,4,9,10-bisfuroxano- 5,1 1-dehydro-5H,11H-benzotriazolo(2,1-alpha)benzotriazole 11. From this study the first of a new class of insensitive energetic materials 4 has been synthesized in a straightforward fashion from 2. jg