Neber rearrangement

The Neber rearrangement is an organic reaction in which a ketoxime is converted into an alpha-aminoketone via a rearrangement reaction.{{JerryMarch}}{{cite journal

| author = P. W. Neber and A. v. Friedolsheim

| journal = Justus Liebig's Annalen der Chemie

| volume =449

| issue = 1

| year = 1926

| title = Über eine neue Art der Umlagerung von Oximen

| pages = 109–134

| doi = 10.1002/jlac.19264490108}}

{{cite journal|last1=O'Brien|first1=Connor|title=The Rearrangement of Ketoxime O-Sulfonates to Amino Ketones (The Neber Rearrangement)|journal=Chemical Reviews|date=1 April 1964|volume=64|issue=2|pages=81–89|doi=10.1021/cr60228a001}}

: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.{{Citation |last=Uyanik |first=M. |title=6.14 Functional Group Transformations via Carbonyl Derivatives |date=2014-01-01 |url=https://www.sciencedirect.com/science/article/pii/B9780080977423006224 |work=Comprehensive Organic Synthesis (Second Edition) |pages=573–597 |editor-last=Knochel |editor-first=Paul |place=Amsterdam |publisher=Elsevier |language=en |isbn=978-0-08-097743-0 |access-date=2022-10-10 |last2=Ishihara |first2=K.}}