Oxymercuration Reaction - Other Applications

Other Applications

Oxymercuration is not limited to an alkene reacting with water. Using an alkyne instead of an alkene yields an enol, which tautomerizes into a ketone. Using an alcohol instead of water yields an ether. In both cases, Markovnikov's rule is observed.

Using a vinyl ether in the presence of an alcohol allows the transfer of the alkoxy group (RO-) from the alcohol to the ether. An allyl alcohol and a vinyl ether under the conditions of oxymercuration reaction can give R-CH=CH-CH2-O-CH=CH2, which is suitable for a Claisen Rearrangement.

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