Chemical Sciences: A Manual for CSIR-UGC National Eligibility Test for Lectureship and JRF/Named Reactions/Sommelet-Hauser Rearrangement

The Sommelet-Hauser rearrangement is a rearrangement reaction of certain benzyl quaternary ammonium salts. The reagent is sodium amide or another alkali metal amide and the reaction product a N-dialkyl benzyl amine with a new alkyl group in the aromatic ortho position.


 * SommeletHauserReaction.svg

This reaction was named after M. Sommelet and Charles R. Hauser

Mechanism
The benzylic methylene proton is acidic and deprotonation takes place to the ylide. The second step is a 2,3-sigmatropic rearrangement.


 * SommeletHauserMechanism.svg