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Sommelet–Hauser rearrangement

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Title: Sommelet–Hauser rearrangement  
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Subject: Quaternary ammonium cation, 2,3-sigmatropic rearrangement, Stevens rearrangement
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Sommelet–Hauser rearrangement

The Sommelet–Hauser rearrangement (named after M. Sommelet[1] and Charles R. Hauser[2]) is a rearrangement reaction of certain benzyl quaternary ammonium salts.[3][4] 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.


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

The Stevens rearrangement is a competing reaction.


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