Neber rearrangement

The Neber rearrangement is an organic reaction in which an oxime is converted into an alpha-aminoketone in a rearrangement reaction.

The oxime is first converted to a ketoxime 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.

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