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