Abstract
Nitrolysis of 2,6,8,12-tetraacetyl-4,10-dibenzyl-2,4,6,8,10,12-hexaazatetracyclo-[5.5.0.03,11.05,9]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[5.5.0.03,11.05,9]-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[5.5.0.03,11.05,9]dodecane under similar conditions.
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Kalashnikov, A.I., Sysolyatin, S.V., Sakovich, G.V. et al. Nitrolysis of 2,6,8,12-tetraacetyl-4,10-dibenzyl-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane. Russ Chem Bull 66, 531–536 (2017). https://doi.org/10.1007/s11172-017-1767-y
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DOI: https://doi.org/10.1007/s11172-017-1767-y