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Rearrangement of N-(3-pyridyl)nitramine

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Abstract

Contrary to other N-(pyridyl)nitramines, the title compound cannot be rearranged to 3-amino-2-nitropyridine or other isomers. Hypothetical products of its transformation under influence of concentrated sulphuric acid, viz. 3-hydroxypyridine, 3,3′-azoxypyridine and 3,3′-azopyridine, were obtained from 3-nitro- and 3-aminopyridine in oxidation and reduction reactions. N-(3-Pyridyl)nitramine was prepared and rearranged in concentrated sulphuric acid. 3-Hydroxypyridine and 3,3′-azoxypyridine were isolated from the reaction mixture, other products were identified by the HPLC and GCMS methods. The results indicate that N-(3-pyridyl)hydroxylamine is an intermediate formed from N-(3-pyridyl)nitramine under the influence of concentrated sulphuric acid. The reaction path, leading to the final products, is discussed in context of the mechanism of nitramine rearrangement.

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  1. Institute of Chemistry, University of Opole, 45-052, Opole, Oleska 48, Poland

    Grzegorz P. Spaleniak, Zdzisław Daszkiewicz & Janusz B. Kyzioł

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  1. Grzegorz P. Spaleniak
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  2. Zdzisław Daszkiewicz
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  3. Janusz B. Kyzioł
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Correspondence to Grzegorz P. Spaleniak.

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Spaleniak, G.P., Daszkiewicz, Z. & Kyzioł, J.B. Rearrangement of N-(3-pyridyl)nitramine. Chem. Pap. 63, 313–322 (2009). https://doi.org/10.2478/s11696-008-0099-7

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