Amine-aldehyde condensation reaction of tetraacetylhexaazaisowurtzitane

Tetraacetylhexaazaisowurtzitane (TAIW), the precursor to CL-20, was condensed with formaldehyde, acetaldehyde or chloroacetaldehyde, and three new isowurtzitane derivatives, 3, 5, 9, 11-tetraacetyl-14-oxo-1, 3, 5, 7, 9, 11-hexaazapentaacyclo-[5.5.3.0^2,6. 0^4,100^8,12] pentadecane, 13, 15-dimethyl-3, 5, 9, 11-tetraacetyl-14-oxo-1, 3, 5, 7, 9, 11-hexaazapentaacyclo [5.5.3.0^2,6. 0^4-100^8,12] pentadecane and 13, 15-dichloromethyl-3, 5, 9, 11-tetraacetyl-14-oxo-1, 3, 5, 7, 9, 11-hexaazapentaacyclo [5.5.3.0^2,6. 0^4,100^8,12] pentadecane, were synthesized and structurally characterized by elemental analysis, IR, ¹H NMR, ¹³C NMR and MS. The results show that characteristics of the proton spectra of this new type caged compound are two signals at δ=6.2 and 5.4 in a 2:1 ratio. The three new compounds may be used as potential precursors of new energetic materials.