Oxymercuration reaction

In organic chemistry, the oxymercuration reaction is a chemical reaction that uses mercury salts transforms an alkene (R2C=CR2) into an alcohol. The alkene reacts with mercuric acetate (AcO−Hg−OAc), an electrophile, to yield an organomercury compound, which is subsequently transformed. The intermediate features an acetoxymercury (−HgOAc) group and a hydroxy (−OH) group attached to adjacent carbon atoms. Carbocations are not formed in this process, and thus rearrangements are not observed. The reaction follows Markovnikov's rule (the hydroxy group always add to the more substituted carbon). The oxymercuration part of the reaction involves anti addition of OH group. On the other hand, the demercuration part of the reaction involves free radical mechanism and is not stereospecific, i.e. H and OH may be syn or anti to each other.

Oxymercuration followed by reductive demercuration is called an oxymercuration–reduction reaction or oxymercuration–demercuration reaction. This reaction, which is almost always done in practice instead of oxymercuration, is treated at the conclusion of the article.

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