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Rearrangement of N -(3-pyridyl)nitramine
Spaleniak, Grzegorz P., Daszkiewicz, Zdzisław and Kyzioł, Janusz B. Rearrangement of N -(3-pyridyl)nitramine Chemical Papers, Vol.63, No. 3, 2009, 313-322
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Document type:
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Článok z časopisu / Journal Article |
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Collection:
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Chemical papers
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| Author(s) |
Spaleniak, Grzegorz P.
Daszkiewicz, Zdzisław
Kyzioł, Janusz B.
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| Title |
Rearrangement of N -(3-pyridyl)nitramine
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| Journal name |
Chemical Papers
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| Publication date |
2009
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| Year available |
2009
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| Volume number |
63
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| Issue number |
3
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| ISSN |
0366-6352
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| Start page |
313
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| End page |
322
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| Place of publication |
Poland
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| Publisher |
Versita
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| Collection year |
2009
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| Language |
english
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| Subject |
250000 Chemical Sciences
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| Abstract/Summary |
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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