78019-97-3Relevant articles and documents
Studies of Tertiary Amine Oxides. Part 7. Solvent effects on the Rearrangement of N-Arylamine Oxides to O-Arylhydroxylamines. The SNi Mechanism
Khuthier, Abdul-Hussain,Al-Mallah, Khawla Y.,Hanna, Salim Y.
, p. 413 - 418 (2007/10/02)
The rate of rearrangement of N-arylamine oxides (4) to O-arylhydroxylamines (5) was measured in different solvents.The rate of isomerisation of p-nitrophenyl N-oxides correlates with the dielectric constants of aprotic solvents and with the hydrogen-bonding ability of protic solvents.The rearrangement of o-nitrophenyl N-oxides shows much less variation in rate with solvent polarity.All kinetic results are explained in terms of an intramolecular cyclic mechanism (SNi).
Studies of Tertiary Amine Oxides. 4. Thermal Rearrangement of N-Aryl Amine Oxides to O-Arylhydroxylamines
Khuthier, Abdul-Hussain,Al-Kazzaz, Abdul-Khalik S.,Al-Rawi, Jasim M. A.,Al-Iraqi, Mohammed A.
, p. 3634 - 3638 (2007/10/02)
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.