Polychloroaromatic compounds. Part I. Oxidation of pentachloropyridine and its NN-disubstituted amino-derivatives with peroxyacids
- 1 January 1968
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 1537-1541
- https://doi.org/10.1039/j39680001537
Abstract
Oxidation of NN-disubstituted 2-aminotetrachloropyridines with peroxyacids yields the corresponding NNO-trisubstituted hydroxylamines and not the expected N-oxides. These hydroxylamines eliminate the NN-disubstituted amino-group when warmed in solvents or when irradiated, and form polychloro-2-pyridones. The influence of substituents on this rearrangement and its mechanism are discussed. The NN-disubstituted 4-aminopyridines rearrange only under forcing conditions to hydroxylamines which do not, however, undergo fragmentation when heated.Keywords
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