Sommelet-Hauser Rearrangement

M. Sommelet, Compt. Rend. 205, 56 (1937).

Rearrangement of benzyl quaternary ammonium salts to ortho substituted benzyldialkylamines on treatment with alkali metal amides:

Early reviews: H. E. Zimmerman in Molecular Rearrangements Part 1, P. de Mayo, Ed. (Wiley-Interscience, New York, 1963) pp 382-391; S. H. Pine, Org. React. 18, 403-464 (1970). Extension to sulfur ylides: M. Yamamoto et al., Bull. Chem. Soc. Japan 62, 958 (1989); H. Ishibashi et al., Chem. Pharm. Bull. 39, 2878 (1991). Effects of aromatic substitution: T. Tanaka et al., ibid. 40, 518 (1992). Selectivity studies (Sommelet-Hauser rearrangement vs Stevens rearrangement, q.v.): T. Kitano et al., J. Chem. Soc. Perkin Trans. I 1992, 2851; T. Tanaka et al., J. Org. Chem. 57, 5034 (1992). Cf. Meisenheimer Rearrangements; [2,3]-Wittig Rearrangement.