Tiffeneau-Demjanov Rearrangement

M. Tiffeneau et al., Compt. Rend. 205, 54 (1937).

Rearrangement of β-amino alcohols upon diazotization with nitrous acid to give carbonyl compounds. Cyclic alcohols yield ring expanded or contracted products:

Reviews: P. A. S. Smith, D. R. Baer, Org. React. 11, 157-188 (1960); H. Metzger, Houben-Weyl 10/4, 233 (1968); D. J. Coveney, Comp. Org. Syn. 3, 781-782 (1991). W. E. Parham, C. S. Roosevelt, J. Org. Chem. 37, 1975 (1972); D. Fattori et al., Tetrahedron 49, 1649 (1993). Cf. Demjanov Rearrangement; Pinacol Rearrangement.