Neber rearrangement

The Neber rearrangement is a name reaction in organic chemistry. It is used to produce α -amino ketones from ketones.

Reaction mechanism

For this purpose, the ketone is first reacted with hydroxylamine to give the oxime. The oxygen atom of the oxime is then reacted with p-toluenesulfonyl chloride to tosylate. Deprotonation of the hydroxy group is a base, such as pyridine are used. The tosylated oxime thus obtained is reacted in the next step with a strong base, which removes the C, H -acidic proton in α -position to the oxime. Suitable bases are, for example, alkoxides such as sodium methoxide or sodium ethoxide. The carbanion thus formed then accesses the nucleophilic nitrogen of the oxime applied, and the tosylate ion, as a good leaving group exits the molecule. The derivative thus formed can then be hydrolysed the azirine to give the desired aminated ketone formed.

Swell

• L. M. Harwood: polar surroundings. 1st edition, VCH Weinheim 1995, ISBN 3-527-29291-8.