Hofmann Reaction

A. W. Hofmann, Ber. 14, 2725 (1881).

Conversion of primary carboxylic amides to primary amines with one fewer carbon atom upon treatment with hypohalites or hydroxide via the intermediate isocyanate:



Early review: E. S. Wallis, J. F. Lane, Org. React. 3, 267-306 (1949). Alternative reagents/strategies: S. Kajigaeshi et al., Chem. Letters 1989, 463; S. Jew et al., Arch. Pharm. Res. 15, 333 (1992); D. S. Rane, M. M. Sharma, J. Chem. Tech. Biotechnol. 59, 271 (1994); H. Moustafa et al., Tetrahedron 53, 625 (1997); Y. Matsumura et al., J. Chem. Soc. Perkin Trans. I 1999, 2057. Review: T. Shioiri, Comp. Org. Syn. 6, 800-806 (1991). Cf. Curtius Rearrangement; Lossen Rearrangement; Schmidt Reaction; Weerman Degradation.