Because of its reactivity, malonic acid diamide (1) was initially identified as an alternative precursor for the development of a new class of high-density insensitive energetic materials possessing low sensitivity to thermal decomposition and detonation by impact. Nitration of 1 was studied under different conditions and led to three different tautomeric forms (2-4) of nitromalonic acid diamine. Using stronger oxidation conditions the oxadiazole 5 was generated in one step. We report the full 1H, 13C and 15N NMR structural characterization of these compounds in DMSO together with thermal, infrared, mass spectrometric and x-ray analysis. Experimental data obtained for 4 are compatible with an enol-imine form. Our interpretation is consistent with calculated 1H and 13C NMR spectra (ACD).
Copyright 2005 John Wiley & Sons, Ltd