Woodward cis-Hydroxylation

R. B. Woodward, US 2687435 (1954); R. B. Woodward, F. V. Brutcher, J. Am. Chem. Soc. 80, 209 (1958).

The hydroxylation of an olefin with iodine and silver acetate in wet acetic acid to give cis-glycols:

L. B. Barkley, M. W. Farrar, J. Am. Chem. Soc. 76, 5014, (1954); W. S. Knowles, Q. E. Thompson, ibid. 79, 3212 (1957); W. F. Forbes, R. Shelton, J. Org. Chem. 24, 436 (1959); F. D. Gunstone, Adv. Org. Chem. 1, 117 (1960). Application to steroids: L. Mangoni, V. Dovinola, Tetrahedron Lett. 1969, 5235; P. Kocovsky, V. Cerny, Collect. Czech. Chem. Commun. 42, 163 (1977). Modification: L. Mangoni et al., Gazz. Chim. Ital. 105, 377 (1975). Cf. Prévost Reaction.