Meisenheimer Rearrangement

Abstract

The tertiary aliphatic amine oxides (tertiary N ‐oxides) undergo to thermal transformation into substituted N ‐alkoxylamines or N ‐hydroxylamines, and generally referred to as the Meisenheimer rearrangement. The study finds that this reaction takes place through a radical mechanism involving a homolytic cleavage of a nitrogen‐carbon bond and the migration of an alkyl group to form the N ‐alkoxylamine. This rearrangement does not apply to aromatic N ‐oxides. The reaction mechanism for such rearrangement has been discussed for aryl allyl N ‐oxides, N ‐propargylmorpholine N ‐oxide and N ‐propargylmorpholine N ‐oxide. This reaction has been found to be useful for organic synthesis.