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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 a hydroxy (−OH) group across the ...
The Hg 2+ center binds to alkenes, inducing the addition of hydroxide and alkoxide. For example, treatment of methyl acrylate with mercuric acetate in methanol gives an α-mercuri ester: [6] Hg(OAc) 2 + CH 2 =CHCO 2 CH 3 + CH 3 OH → CH 3 OCH 2 CH(HgOAc)CO 2 CH 3 + HOAc. Exploiting the high affinity of mercury(II) for sulfur ligands, Hg(OAc) 2 ...
[2] [3] [4] However, unlike sodium cyanoborohydride, the triacetoxyborohydride hydrolyzes readily, nor is it compatible with methanol. It reacts only slowly with ethanol and isopropanol and can be used with these. [3] Reductive amination with STAB. NaBH(OAc) 3 may also be used for reductive alkylation of secondary amines with aldehyde-bisulfite ...
Sodium borohydride can, under some circumstances, be used for ester reduction, especially with additives. [ 1 ] Forming aldehydes from carboxylic acid derivatives is challenging because weaker reducing agents (NaBH 4 ) are often very slow at reducing esters and carboxylic acids, whereas stronger reducing agents (LiAlH 4 ) immediately reduce the ...
Since sodium cyanoborohydride is a mild reducing agent, it gives good chemoselectivity for reaction with certain functional groups in the presence of others. For example, sodium cyanoborohydride is generally incapable of reducing amides, ethers, esters and lactones, nitriles, or epoxides. [8]
Through a variety of mechanisms, the removal of a hydride equivalent converts a primary or secondary alcohol to an aldehyde or ketone, respectively. The oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate ( gem -diol, R-CH(OH) 2 ) by reaction with water.
Sodium amalgam, with the common formula Na(Hg), is an alloy of mercury and sodium. The term amalgam is used for alloys, intermetallic compounds, and solutions (both solid solutions and liquid solutions) involving mercury as a major component. Sodium amalgams are often used in reactions as strong reducing agents with better handling properties ...
Rhodium(II) acetate is the coordination compound with the formula Rh 2 (AcO) 4, where AcO − is the acetate ion (CH 3 CO − 2). This dark green powder is slightly soluble in polar solvents, including water. It is used as a catalyst for cyclopropanation of alkenes. It is a widely studied example of a transition metal carboxylate complex. [2]