Iodine-silver acetate

These olefins were transformed into unsaturated acetates by Woodward s protocol with iodine, silver acetate, and acetic acid. Saponification and subsequent oxidation of the liberated alcohols with Collin s reagent resulted in a 2 1 mixture of conjugated enones, 162 and 163, in mediocre yields (Scheme 16). The minor enone 163 was transformed into the cyanoketone 164 by 1,4-addition using... 

Syn hydroxylation from the more hindered face of a ir-system can be effected using Woodward s pro-cedure in which an alkene is treated with iodine-silver acetate in acetic acid containing water. Variants of this method avoid the use of silver salts.A versatile pocedure by which syn hydroxyla-tion can be performed on either the more hindered or less hindered face of an alkene relies on stereoselective formation of the appropriate traru-bromohydrin from the alkene. ... 

Addition to the 22 23)-douUe bond of ergosterol. Iodine-silver acetate in moist acetic acid, a typical electrophilic reagent, reacts with 3oi,Sa-cycloergosta-7,22-diene-... 

Woodward, R. B., Brutcher, F. V., Jr. Cis hydroxylation of a synthetic steroid intermediate with iodine, silver acetate, and wet acetic acid. J. 

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