ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Thermal Rearrangement of Pyridylnitramines

Z. Daszkiewicz, A. Domański, and J. B. Kyziol

Thermal Rearrangement of Pyridylnitramines

Abstract: N-Methyl-N-pyridylnitramines form corresponding methylamino-nitropyridines in 74-90 % yield when heated (120-130°C) in chlorobenzene without an acidic catalyst. N-(P-Pyridyl) nitramine behaves analogously while remaining primary pyridylnitramines rather decompose than rearrange. The rearrangement can he carried out in the anisole or m-xylene solutions without cross-nitration, hence migration of the nitro group must have an intramolecular character. Some analogies in the thermal and acid-catalyzed rearrangements have been observed. Various ortho/para ratios can be explained assuming different mechanisms of hydrogen transfer in the intermediary sigma-complexes.

Full paper in Portable Document Format: 511a22.pdf

Chemical Papers 51 (1) 22–28 (1997)