Sommelet–Hauser rearrangement

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.

Sommelet–Hauser rearrangement

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.