2,4,8, 10-Tetranitrobenzotriazolo[2, 1-alpha]benzotriazole (TACOT), al
though thermally very stable and insensitive as an explosive, is susce
ptible to attack by nucleophiles. Reaction with azide ion results in d
isplacement of nitro groups at the 4,10-positions, treatment with meth
oxide ion effects displacement of the hydrogen atom at the 1-position
and scission of the remote triazole ring, while ''vicarious nucleophil
ic amination'' displaces all the aromatic hydrogens. 3,5,7-Trinitro-1,
3,3-triazolo[2, 1-alpha]benzotriazole and ,7-trinitro-1,2,3-triazolo[1
,2-alpha]benzotriazole are prepared readily by nitration of the parent
triazolobenzotriazoles. However they are thermally less stable than T
ACOT and more sensitive to initiation by impact. Furthermore, attempte
d further nitration and reaction with nucleophiles such as azide and m
ethoxide ions both effect scission of the triazole ring to leave 4,6-d
initrobenzotriazole.