Demjanov Rearrangement

N. J. Demjanov, M. Lushnikov, J. Russ. Phys. Chem. Soc. 35, 26 (1903); Chem. Zentr. 1903, 1, 828.

Deamination of primary amines by diazotization to give rearranged alcohols. In the case of alicyclic amines, ring enlargement or contraction occurs:



P. A. S. Smith, D. R. Baer, Org. React. 11, 157 (1960); H. Stetter, P. Goebel, Ber. 96, 550 (1963); R. Kotani, J. Org. Chem. 30, 350 (1965); V. Dave et al., Can. J. Chem. 57, 1557 (1979); R. K. Murray, Jr., T. M. Ford, J. Org. Chem. 44, 3504 (1979); D. Fattori, et al., Tetrahedron 49, 1649 (1993). Cf. Tiffeneau-Demjanov Rearrangement; Wagner-Meerwein Rearrangement.