SYSTEMATIC SUBSTITUTION ON THE CUBANE NUCLEUS - SYNTHESIS AND PROPERTIES OF 1,3,5-TRINITROCUBANE AND 1,3,5,7-TETRANITROCUBANE

A systematic methodology is developed for the synthesis of highly symmetric, polysubstituted cubanes. The synthesis of cubanes with C3v and T(d) symmetry is achieved. Details are given for the preparation of 1,3,5-trinitrocubane and 1,3,5,7-tetranitrocubane, compounds of interest as superior high-energy, shock-insensitive explosives. The structures of these new materials, determined by single-crystal X-ray analysis, are discussed in detail. DSC analysis of their thermal decomposition is presented. The effect of nitro groups on the C-13-NMR spectra of cubanes is noted.