Abstract
Mercury(II) acetate is a commercially available reagent which can be prepared by the reaction of elemental mercury with peroxyacetic acid.[ 1 ] The standard use of this reagent is the textbook oxymercuration–demercuration reaction, an electrophilic addition in which mercury(II) acetate attacks a double bond forming a mercury–olefin complex, followed by nucleophilic ring opening with water and subsequent reductive demercuration with sodium borohydride.[ 2 ] The reaction proceeds in accordance with Markovnikov‘s rule, since the nucleophilic reagent attacks the higher substituted carbon atom to form the more stable carbocation intermediate. This reaction is also an anti-addition: the nucleophilic reagent attacks the double bond–mercury complex from the side opposite to the molecule.
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