Woodward cis-hydroxylation

The Woodward cis-hydroxylation is the chemical reaction of alkenes with iodine and silver acetate in wet acetic acid to form cis-diols.^[1][2] The reaction is named after its discoverer, Robert Burns Woodward.

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This reaction has found application in steroid synthesis.^[3]

Reaction mechanism

The reaction of the iodine with the alkene is catalyzed by the silver acetate, thus forming an iodinium ion (3). The iodinium ion is opened via S_N2 reaction by acetic acid (or silver acetate) to give the first intermediate, the iodo-acetate (4). Through anchimeric assistance, the iodine is displaced via another S_N2 reaction to give an oxonium ion (5), which is subsequently hydrolyzed to the give the mono-ester (6).

The mono-ester can be hydrolyzed using potassium hydroxide to form the corresponding diol.

References

See also

• Prévost reaction