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,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.[2] 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.

  1. ^ M. Sommelet, Compt. Rend. 205, 56 (1937).
  2. ^ a b Rearrangements of Benzyltrimethylammonium Ion and Related Quaternary Ammonium Ions by Sodium Amide Involving Migration into the Ring Simon W. Kantor, Charles R. Hauser J. Am. Chem. Soc., 1951, 73 (9), pp 4122–4131 doi:10.1021/ja01153a022
  3. ^ March, Jerry (1985). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.). New York: Wiley. ISBN 9780471854722. OCLC 642506595.
  4. ^ Organic Syntheses, Coll. Vol. 4, p.585 (1963); Vol. 34, p.61 (1954) Link.
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