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Oxymercuration reaction [1] In organic chemistry , the oxymercuration reaction is an electrophilic addition reaction that transforms an alkene ( R 2 C=CR 2 ) into a neutral alcohol . In oxymercuration, the alkene reacts with mercuric acetate ( AcO−Hg−OAc ) in aqueous solution to yield the addition of an acetoxymercury ( −HgOAc ) group and ...
The general chemical equation for the hydration of alkenes is the following: RRC=CH 2 + H 2 O → RRC(OH)-CH 3. A hydroxyl group (OH −) attaches to one carbon of the double bond, and a proton (H +) adds to the other. The reaction is highly exothermic. In the first step, the alkene acts as a nucleophile and attacks the proton, following ...
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.
Formation of a secondary alcohol via alkene reduction and hydration is shown: The hydroboration-oxidation and oxymercuration-reduction of alkenes are more reliable in organic synthesis. Alkenes react with N -bromosuccinimide and water in halohydrin formation reaction .
[6] [12] Treatment of the intermediate silylperoxide with 1 drop of concentrated HCl in methanol leads to the hydroperoxide product. Isayama's work with modp ligand detailed. Both Mukaiyama [13] and Magnus [14] describe conditions for an α-enone hydroxylation reaction using Mn(dpm) x in the presence of oxygen and phenylsilane. An asymmetric ...
One attractive feature of the Peterson olefination is that it can be used to prepare either cis- or trans-alkenes from the same β-hydroxysilane. Treatment of the β-hydroxysilane with acid will yield one alkene, while treatment of the same β-hydroxysilane with base will yield the alkene of opposite stereochemistry.
Hydroboration of 1,2-disubstituted alkenes, such as a cis or trans olefin, produces generally a mixture of the two organoboranes of comparable amounts, even if the steric properties of the substituents are very different. For such 1,2-disubstituted olefins, regioselectivity can be observed only when one of the two substituents is a phenyl ring.
The Bamford–Stevens reaction has not proved useful for the stereoselective generation of alkenes via thermal decomposition of metallated tosylhydrazones due to the indiscriminate 1,2-rearrangement of the carbene center, which gives a mixture of products. By replacing an alkyl group with a trimethylsilyl (TMS) group on N-aziridinylimines ...