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.
^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.