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
- ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition, New York: Wiley, ISBN 9780471854722, OCLC 642506595
- ^ 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.
- ^ 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
 | This chemical reaction article is a stub. You can help Wikipedia by expanding it. |
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
- ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition, New York: Wiley, ISBN 9780471854722, OCLC 642506595
- ^ 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.
- ^ 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
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