Sensitive 1,4-Disubstituted Nitro-Containing Cubanes: Structures and Properties

The cubane cage system is characteristic and well known for its high strain energy, qualifying it as a promising precursor for energetic materials. 1,4-Disubstituted cubanes are the easiest accessible derivatives. A further developed laboratory-scale procedure for cubane-1,4-dicarboxylic acid dimethyl ester is presented. From this central precursor, the bis-trinitroethyl and bis-nitromethyl esters as well as the bis-methylcarbamate and bis-methylnitrocarbamate were synthesized and characterized by multinuclear NMR spectroscopy and X-ray crystallography. In addition, their physical and energetic properties were determined and studied.