Nitrolysis of 2,6,8,12-tetraacetyl-4,10-dibenzyl-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.0 3,11 .0 5,9 ]dodecane

Nitrolysis of 2,6,8,12-tetraacetyl-4,10-dibenzyl-2,4,6,8,10,12-hexaazatetracyclo-[5.5.0.0 3,11 .0 5,9 ]dodecane results in the substitution of benzyl groups by the nitro groups with the formation of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.0 3,11 .0 5,9 ]-dodecane. The reaction sequentially proceeds through the nitration of the benzyl groups predominantly at para -position, the substitution of one nitrobenzyl group with the nitro group, and the introduction of the second nitro group into the nitrobenzyl fragment. The replacement of the remaining dinitrobenzyl fragment is a more difficult process, which reaches completion only by the end of the nitration. Another reaction product is p -nitrobenzoic acid, which is formed in the secondary reactions. No substitution of a p -nitrobenzoyl group with the nitro group takes place in the nitration of 2,6,8,12-tetraacetyl-4,10-di( p -nitrobenzoyl)-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.0 3,11 .0 5,9 ]dodecane under similar conditions.