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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]
Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, [5] is an inorganic compound with the formula Na B H 4 (sometimes written as Na[BH 4]). It is a white crystalline solid, usually encountered as an aqueous basic solution. Sodium borohydride is a reducing agent that finds application in papermaking and dye ...
At low pH values, it efficiently reduces aldehydes and ketones. [7] As the pH increases, the reduction rate slows and instead, the imine intermediate becomes preferential for reduction. [ 7 ] For this reason, NaBH 3 CN is an ideal reducing agent for one-pot direct reductive amination reactions that don't isolate the intermediate imine.
Useful reagents for this reaction include formic acid with a hydrogenation catalysis [12] or metal hydrides, which are used to add one mol of hydrogen to the nitrile. For example, sodium borohydride reduces nitriles in alcoholic solvents with a CoCl 2 catalyst or Raney nickel .
Examples of substances that are common reducing agents include hydrogen, carbon monoxide, the alkali metals, formic acid, [1] oxalic acid, [2] and sulfite compounds. In their pre-reaction states, reducers have extra electrons (that is, they are by themselves reduced) and oxidizers lack electrons (that is, they are by themselves oxidized).
Acid chlorides can be reduced to give aldehydes with sterically hindered hydride donors. The reducing agent DIBAL-H (diisobutylaluminium hydride) is often used for this purpose, although it normally reduces any carbonyl. DIBAL-H can selectively reduce acid chlorides to the aldehyde level if only one equivalent is used at low temperatures. [12]