Oxymercuration reaction

The oxymercuration reaction is an electrophilic addition organic reaction that transforms an alkene into a neutral alcohol. In oxymercuration, the alkene reacts with mercuric acetate (AcO–Hg–OAc) in aqueous solution to yield the addition of an acetoxymercuri (HgOAc) group and a hydroxy (OH) group across the double bond.

Quotes

 * In the laboratory, alkenes are often hydrated by the oxymercuration–demercuration procedure. … Alkene oxymercuration is closely analogous to halohydrin formation.
 * John McMurry, Organic Chemistry 8th ed. (2012), Ch. 8 : Alkenes: Reactions and Synthesis.


 * Treatment of an alkene with mercuric acetate in aqueous THF results in the electrophilic addition of mercuric ion to the double bond to form an intermediate mercurium ion. Nucleophilic attack by H2O at the more substituted carbon yields a stable organomercury compound, which upon addition of NaBH, undergoes reduction. Replacement of the carbon-mercury bond by a carbon-hydrogen bond during the reduction step proceeds via a radical process. The overall reaction represents Markovnikov hydration of a double bond, which contrasts with the hydroboration-oxidation process.
 * George S. Zweifel and Michael H. Nantz, Modern Organic Synthesis (2006), Ch. 5 : Functional Group Transformations: The Chemistry of Carbon-Carbon π-Bonds and Related Reactions.