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.

References[]

^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, 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:10.1002/jlac.19264490108.
^ 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.

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[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.

[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.

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