Evidence for the intermolecular nature of the Meisenheimer rearrangement of amine N-oxides

Abstract

Thermolysis of mixtures of structurally similar amine N-oxides leads to intermolecular rearrangement products, thus calling into question the previously favoured intramolecular mechanism as the exclusive process for the Meisenheimer rearrangement; the results are consistent with a mechanism involving homolytic fission to intermediates which recombine to produce the N-alkoxy-amines.