REACTIONS OF BENZOTRIAZOLO[2,1-ALPHA]BENZOTRIAZOLE DERIVATIVES .1. SYNTHESIS OF NEW INSENSITIVE HIGH-DENSITY ENERGETIC COMPOUNDS

The sequential preference of electrophilic attack on the dibenzotetraa zapentalene ring system 6 has unequivocally been shown to be in the or der of position 2(8) > 4(10) much greater than 1(7) and 3(9). However, nucleophilic substitution reactions with sodium azide were found to b e 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 8(10)-nitro group of 2 was found to yiel d 13. The reactivity of the dibenzotetraazapentalene derivatives towar d electrophiles and nucleophiles was exploited for the synthesis of th e new heterocyclic system ,4':4,5]benzotriazolo[2,1-alpha]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.