Neber rearrangement

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The Neber rearrangement is an organic reaction in which an oxime is converted into an alpha-aminoketone in a rearrangement reaction.[1][2]

Neber rearrangement

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 an azirine and added water subsequently hydrolyses it to the aminoketone.

The Beckmann rearrangement is a side reaction.

References[edit]

  1. ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, ISBN 0-471-85472-7 
  2. ^ 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:10.1002/jlac.19264490108.