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Klapötke, Thomas M.; Krumm, Burkhard; Reith, Thomas; Unger, Cornelia C. (2018): Synthetic Routes to a Triazole and Tetrazole with Trinitroalkyl Substitution at Nitrogen. In: Journal of Organic Chemistry, Vol. 83, No. 17: pp. 10505-10509
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Abstract

Two N-substituted trinitroalkyl azoles, one triazole, and one tetrazole were synthesized and isolated via efficient cyclization reactions. Both materials were thoroughly characterized, and their structures were confirmed by X-ray diffraction. The formation of the N-trinitroethyl substituted triazole proceeds unexpectedly via nitrosation of an N-substituted diaminomaleonitrile initially with HNO3 and subsequently confirmed with HNO2. The N-trinitropropyl substituted tetrazole was prepared via a standard cyclization route from trinitropropylammonium chloride with orthoformate and azide.