Nickel carbonyl-Sodium methoxide

Cathodic surfaces of finely divided platinum, palladium and nickel have a low hydrogen overvoltage and the dominant electrochemical reaction is the generation of a layer of hydrogen atoms. The electrocatalytic hydrogenation of aldehydes and ketones can be achieved at these surfaces. Cathodes of platinum or palladium black operate in both acid solution [203] and in methanol containing sodium methoxide [204], The carbonyl compound is converted to the alcohol. Reduction of 4-tert-butylcyclohexanone is not stereoselective, however, 1,2-diphenylpropan-l-one is converted to the / reo-alcohol. 

A plausible mechanism for the reaction includes several organometallic species that are sensitive to reactive moieties elsewhere in the molecule. If a chloro, chloromethyl, or mesyloxymethyl substituent is attached vicinal to the 1,1 -dibromo moiety, efficient ring opening occurs prior to carbonylation and P,y- and y, -unsaturated acid derivatives are formed. Reductive carbonylation has also been achieved with 1,1-dibromocyclopropanes using an excess of pentacarbonyliron in dimethylformamide with added methanol or sodium methoxide, or cobalt(II) chloride and nickel(ll) cyanide under phase-transfer conditions in a carbon monoxide atmosphere. However, the yield of cyclopropanecarboxylic acid derivatives is low, and when pentacarbonyliron is used the amount of monobromides is fairly high. ... 

Cyclizatton Boron trifluoride etherate. Ion-exchange resin. Lithium, diethylamide. Mercuric acetate(then sodium borohydride). Methanesulfonic acid. Nickel carbonyl. Polyphosphate ester. Sodium aluminum chloride. Sodium methoxide. Trifluoracetic acid. 

Carboxylation of organic halides.5 Vinyl halides when treated with several equivalents of nickel carbonyl in methanol containing 2-3 equiv. of sodium or potassium methoxide are converted into the corresponding methyl esters. The... 

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