Neber rearrangement
From Wikipedia, the free encyclopedia
The Neber rearrangement is an organic reaction in which an oxime is converted into an alpha-aminoketone in a rearrangement reaction.[1][2]
The oxime is first converted to a ketoxime tosylate by reaction with tosyl chloride. Added base forms a carbanion which displaces the tosylate group in a nucleophilic displacement to a azirine and added water subsequently hydrolyses it to the aminoketone.
The Beckmann rearrangement is a side reaction.
[edit] References
- ^ March, Jerry (1985). Advanced Organic Chemistry, Reactions, Mechanisms and Structure, third Edition, John Wiley & Sons. ISBN 0-471-85472-7.
- ^ P. W. Neber and A. v. Friedolsheim (1926). "Über eine neue Art der Umlagerung von Oximen". Justus Liebig's Annalen der Chemie 449 (1): 109-134. doi:.
