Studies of tertiary amine oxides. 4. Thermal rearrangement of N-aryl amine oxides to O-arylhydroxylamines

…, AKS Al-Kazzaz, JMA Al-Rawi, MA Al-Iraqi

Index: Khuthier, Abdul-Hussain; Al-Kazzaz, Abdul-Khalik S.; Al-Rawi, Jasim M. A.; Al-Iraqi, Mohammed A. Journal of Organic Chemistry, 1981 , vol. 46, # 18 p. 3634 - 3638

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Citation Number: 18

Abstract

Substituted N-aryl cyclic amine oxides undergo novel thermal rearrangement to 0- arylhydroxylamines. Electron-withdrawing substituents are essential for the rearrangement and must be ortho or para relative to the+ N-0 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- ...