Neber rearrangement

The Neber rearrangement is an organic reaction in which a ketoxime is converted into an alpha-aminoketone via a rearrangement reaction.^[1][2][3]

The oxime is first converted to an O-sulfonate, for example a 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.^[4]

References

1. March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition, New York: Wiley, ISBN 9780471854722, OCLC 642506595
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.
3. O'Brien, Connor (1 April 1964). "The Rearrangement of Ketoxime O-Sulfonates to Amino Ketones (The Neber Rearrangement)". Chemical Reviews. 64 (2): 81–89. doi:10.1021/cr60228a001.
4. Uyanik, M.; Ishihara, K. (2014-01-01), Knochel, Paul (ed.), "6.14 Functional Group Transformations via Carbonyl Derivatives", Comprehensive Organic Synthesis (Second Edition), Amsterdam: Elsevier, pp. 573–597, ISBN 978-0-08-097743-0, retrieved 2022-10-10