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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]
Alkyne oxymercuration-demercuration: In this reaction, HgSO 4 reacts with an alkyne in a Markovnikov regioselective manner to form an enol that is tautomerized into a ketone. This process utilizes anti addition of an OH group to the more substituted carbon, making this reaction a Markovnikov reaction. Alkyne hydroboration-oxidation
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. The hydration of an alkene gives an alcohol.
The reaction thus provides a more stereospecific and complementary regiochemical alternative to other hydration reactions such as acid-catalyzed addition and the oxymercuration–reduction process. The reaction was first reported by Herbert C. Brown in the late 1950s [2] and it was recognized in his receiving the Nobel Prize in Chemistry in 1979.
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 .
Mercury(II) acetate is used for oxymercuration reactions. A famous use of Hg(OAc) 2 was in the synthesis of idoxuridine. Toxicity. Mercuric acetate is a highly toxic ...
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In organic chemistry, the oxy-Cope rearrangement is a chemical reaction.It involves reorganization of the skeleton of certain unsaturated alcohols. It is a variation of the Cope rearrangement in which 1,5-dien-3-ols are converted to unsaturated carbonyl compounds by a mechanism typical for such a [3,3]-sigmatropic rearrangement.