Home  

Random  

Nearby  



Log in  



Settings  



Donate  



About Wikipedia  

Disclaimers  



Wikipedia





Neber rearrangement





Article  

Talk  



Language  

Watch  

Edit  





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

Neber rearrangement

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

edit
  1. ^ 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

  • t
  • e

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Neber_rearrangement&oldid=1165981720"
     



    Last edited on 18 July 2023, at 17:06  





    Languages

     


    العربية
    Čeština
    Deutsch
    Español
    فارسی
    Français
    Bahasa Indonesia
    Italiano

    Polski
    Română
    Русский
    ி
    Українська

     

    Wikipedia


    This page was last edited on 18 July 2023, at 17:06 (UTC).

    Content is available under CC BY-SA 4.0 unless otherwise noted.



    Privacy policy

    About Wikipedia

    Disclaimers

    Contact Wikipedia

    Code of Conduct

    Developers

    Statistics

    Cookie statement

    Terms of Use

    Desktop