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Neber rearrangement

From Wikipedia, the free encyclopedia

TheNeber rearrangement is anorganic reaction in which aketoxime is converted into an alpha-aminoketone via arearrangement reaction.[1][2][3]

Neber rearrangement

The oxime is first converted to an O-sulfonate, for example atosylate by reaction withtosyl chloride. Addedbase forms acarbanion which displaces the tosylate group in anucleophilic displacement to anazirine and added water subsequently hydrolyses it to the aminoketone.

TheBeckmann rearrangement is aside reaction.[4]

References

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  1. ^March, Jerry (1985).Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.). 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, retrieved2022-10-10


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