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RESEARCH PRODUCT
Rearrangement of N-(3-pyridyl)nitramine
Zdzisław DaszkiewiczJanusz B. KyziołGrzegorz Spaleniaksubject
nitramine rearrangementGeneral Chemical EngineeringContext (language use)General Chemistrynitro-to-nitrito transformationazoxypyridinesBiochemistryMedicinal chemistryHigh-performance liquid chromatographyRedoxIndustrial and Manufacturing Engineeringchemistry.chemical_compoundHydroxylaminechemistryazopyridinesMaterials ChemistryOrganic chemistryReaction pathdescription
AbstractContrary 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-01-01 | Chemical Papers |