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In demercuration, the acetoxymercury group is replaced with a hydrogen in a stereochemically insensitive reaction [6] known as reductive elimination. The combination of oxymercuration followed immediately by demercuration is called an oxymercuration–reduction reaction. [7]
Alkene oxymercuration-demercuration: Stereospecific: Can only be anti addition – water kicks out the mercury from underneath the intermediate three-membered ring. The reaction is considered Markovnikov as it results in water addition with same regiospecificity as a direct hydration reaction. Alkene hydroboration-oxidation
Conversion of 2,5-dimethylhexyne-2,5-diol to 2,2,5,5-tetramethylte-trahydrofuran-3-one. Mercury sulfate, as well as other mercury(II) compounds, are commonly used as catalysts in oxymercuration-demercuration, a type of electrophilic addition reaction that results in hydration of an unsaturated compound.
In general oxymercuration reactions of alkenes and alkynes using mercuric compounds proceed via organomercury intermediates. A related reaction forming phenols is the Wolffenstein–Böters reaction .
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