Sommelet–Hauser rearrangement

Overview

The Sommelet–Hauser rearrangement (named after M. Sommelet and Charles R. Hauser) 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,N-dialkylbenzylamine with a new alkyl group in the aromatic ortho position. For example, benzyltrimethylammonium iodide, [(C6H5CH2)N(CH3)3]I, rearranges in the presence of sodium amide to yield the o-methyl derivative of N,N-dimethylbenzylamine. Although the appearance is of one of the methyl groups migrating off the trimethylammonium group, the process is actually the a pericyclic reaction in which the nitrogen and its three methyl substituents migrate.

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