Nitrolysis of 3,5,9,11-tetraacetyl-14-oxo-1,3,5,7,9,11-hexaazapentacyclo[ 5.5.3.0^2,6.0^4,10.0^8,12] pentadecane

In order to develop a new energetic materials, nitrolysis of 3,5,9,11-tetraacetyl-14-oxo-1,3 ,5 ,7 ,9,11-hexaazapentacyclo [5.5. 3. 0^2,6. 0^4,10. 0^8,12] pentadecane (I) was studied in detail. I was nitrolyzed selectively to 4-nitratomethyl-2,6, 8, 12-tetraacetyl-10-nitro-2,4,6,8,10,12-hexaazaisowurtzitane (II) with HNO₃/Ac₂O. While with mixture of nitric and sulfuric acids as nitration reagent, at 80 °C directly or at 15 °C 2 h firstly then 80 °C I was nitrolyzed to CL-20 or 4-nitratomethyl-2,6,8,10,12-pentanitrohezaazaisowurtzitane (III) respectively. II can also be nitrated to HI. The structures of two new hexaazaisowurtzitane derivatives (II and I) were confirmed by MS,IR,¹H NMR and ¹³C NMR.