Tetraazadecalins, structure

The A-nitration of the furazan-based heterocycle (29) has been reported. The corresponding tetranitramine (30) is an unstable substance, but obtained on treating (29) with either trifluoroacetic anhydride (TFAA) in nitric acid or dinitrogen pentoxide in nitric acid. In this case the furazan rings stabilize the 1,4,5,8-tetraazadecalin structure and further reduce the basicity of the amidine amino groups. A number of other furazan and nitrogen-rich nitramines... 

L., Ganguly, B., Fuchs, B. (1998). The 1,3,5,7-tetraazadecalins structure, conformation, and stereoelectronics. Theory vs. experiment. Journal of Organic Chemistry, 63, 8850-8859. (b) Ritter, 1., Gleiter, R., Imgartinger, H., Oeser, T. (1997). Conformations of Azacyclodeca-3,8-diynes and l,6-Diazacyclodeca-3,8-diynes and the Generalized Anomeric Effect A Test for Current Conformational Models for Azaheterocycles. Journal of the American Chemical Society, 119, 10599-10607. 

The results, presented in Table 8, show that in most cases the conformer with the lowest steric energy indeed corresponds to the experimentally most favored one. In addition, several molecules containing the N—C—N moiety were retrieved from the Cambridge Structural Database and calculated with the new parameter set. A comparison between MM2 and X-ray geometries (selected structural parameters only) for two conformers of 1,4,5,8-tetraazadecalin (25, 26) is provided in Table 9 and shows good fit between the experimental and calculated data. 

Trans-l,4,5,8-tetranitro-l,4,5,8-tetraazadecalin (TNAD) [Structure (2.52)] has been obtained by the reaction of trans-1,4,5,8 tetraazadecalin with NaN02 and HC1 to... 

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