Retropinacol Rearrangement

N. Zelinsky, J. Zelikow, Ber. 34, 3249 (1901).

Conversion of an alcohol to the rearranged olefin on treatment with acid:

Application to sterols: W. F. Johns, J. Org. Chem. 26, 4583 (1961); L. M. Harrison, P. V. Fennessey, J. Steroid Biochem. 36, 407 (1990); to cyclohexanols: W. Hueckel, S. K. Gupte, Ann. 685, 105 (1965). In conjunction with ring expansion: T. Kimura et al., J. Org. Chem. 43, 1247 (1978). Cf. Nametkin Rearrangement; Wagner-Meerwein Rearrangement.