Mechanistic Investigations on the Reaction between Amines or Amides and an Alkylperoxy-λ3-iodane
- 15 March 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (8) , 3307-3310
- https://doi.org/10.1021/jo0268005
Abstract
A mechanism involving the intermediate formation of an amine radical cation by single-electron transfer is proposed for the oxidation of secondary amines with alkylperoxy-lambda(3)-iodane. On the other hand, the oxidation of acetamides probably proceeds by a radical process, which involves the direct hydrogen abstraction of the methylene group alpha to the nitrogen atom.Keywords
This publication has 19 references indexed in Scilit:
- Oxidative N-demethylation of N,N-dimethylanilines catalysed by lignin peroxidase: a mechanistic insight by a kinetic deuterium isotope effect studyChemical Communications, 2000
- Quantum Chemical Studies on the Thermochemistry of Alkyl and Peroxyl RadicalsThe Journal of Physical Chemistry A, 1999
- Photoelectron spectroscopy, gas phase acidity, and thermochemistry of tert-butyl hydroperoxide: Mechanisms for the rearrangement of peroxyl radicalsThe Journal of Chemical Physics, 1998
- Mechanism of Oxidative Amine Dealkylation of Substituted N,N-Dimethylanilines by Cytochrome P-450: Application of Isotope Effect ProfilesJournal of the American Chemical Society, 1995
- A stable crystalline alkylperoxyiodinane: 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-oneJournal of the American Chemical Society, 1992
- Oxoammonium Salts. 4 A New Reagent for Phenol CouplingHETEROCYCLES, 1992
- Molar paramagnetic solvent NMR shifts of galvinoxyl in toluene. Kinetics of the reaction between galvinoxyl and tertiary amines at high radical concentrationsMagnetic Resonance in Chemistry, 1990
- Oxidation of N-acyl-pyrrolidines and -piperidines with lron(II)-hydrogen peroxide and an iron complex-molecular oxygenJournal of the Chemical Society, Perkin Transactions 1, 1987
- Electroorganic chemistry. XX. Anodic oxidation of carbamatesJournal of the American Chemical Society, 1975
- Electrophilic Substituent ConstantsJournal of the American Chemical Society, 1958