Reactions of benzotriazolo[2,1-a]benzotriazole derivatives. 1. Synthesis of new insensitive high-density energetic compounds

Article abstract of DOI:10.1021/jo00124a024

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 14H-[1,2,5]oxadiazolo[3,4-e][1,2,5]-oxadiazolo[3',4':4,5]benzotriazolo [2,1-a]benzotriazol-6-ium inner salt 1,8-dioxide (11). From this study the first of a new class of insensitive energetic materials 4 has been synthesized in a straightforward fashion from 2.