MECHANISMS OF THE OXIDATION OF ORGANIC AMINES BY OXYGEN AND BY FREE RADICAL OXIDIZING AGENTS
Abstract
OXIDATION OF Amines by Ozone and other reagents: A study of the oxidation of tributylamine by O3 and MnO2 was made. The oxidation products depended on the reaction conditions. The N-oxide was the main product in some solvents whereas attack of O3 at the C next to N occurred in others. Oxidation of tributylamine with MnO2 gave N-formyldibutylamine; similar oxidation occurs with other trialkylamines. Oxidation of Amines by Monovalent Radicals: Examples of the formation of substituted ethylene diamines by reaction of tertiary amines with t-butoxy radicals are given. Dehydrogenative coupling did not occur when t-butoxy-radicals reacted with dimethylaniline in acetic acid solution. The amine was demethylated, the ejected C linking 2, then 3 aromatic rings together. Evidence for intermediate steps in the over-all reaction was obtained. Reactions of Amines in Aqueous Solution with Polyvalent Metal Oxidants: Argentic compounds are uniquely effective for aliphatic amine oxidations in aqueous media. With aqueous solutions of primary amines, argentic picolinate gave aldehydes or ketones in 10-40% yield, while secondary amines gave yields of 20-90%.
Document Details
- Document Type
- Technical Report
- Publication Date
- Oct 31, 1961
- Accession Number
- AD0269695
Entities
People
- M. J. Stratford
- Robert D. Patton
- W.j. Hanna
Organizations
- Queen Mary University of London