Polychloroaromatic compounds. Part I. Oxidation of pentachloropyridine and its NN-disubstituted amino-derivatives with peroxyacids

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.