Studies of Tertiary Amine Oxides. 4. Thermal Rearrangement of N-Aryl Amine Oxides to O-Arylhydroxylamines

Article abstract of DOI:10.1021/jo00331a010

Substituted N-aryl cyclic amine oxides undergo novel thermal rearrangement to O-arylhydroxylamines.Electron-withdrawing substituents are essential for the rearrangement and must be ortho or para relative to the N->O function.The mechanism of the rearrangement is best described by an intramolecular cyclic process.Kinetic results are in agreement with the cyclic process but are inconsistent with a homolytic dissociation-recombination mechanism.