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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 ...
[3] [4] An example of a transition metal-catalyzed cyclopropanation is a synthesis of tranylcypromine, [5] [6] in which the sodium salt of benzaldehyde tosylhydrazone is converted to a rhodium metal carbene through the diazo intermediate. Tosylhydrazones are also starting materials for certain cross-coupling reactions. [7]
The reaction involving benzaldehyde was discovered by Claisen using sodium benzylate as base. [1] The reaction produces benzyl benzoate. [4] The Tishchenko reaction: benzaldehyde reacts to benzyl benzoate, the catalyst is sodium benzylate. Enolizable aldehydes are not amenable to Claisen's conditions.
The intermediate imine can be isolated or reacted in-situ with a suitable reducing agent (e.g., sodium borohydride) to produce the amine product. [2] Intramolecular reductive amination can also occur to afford a cyclic amine product if the amine and carbonyl are on the same molecule of starting material. [4]
Two equivalents of strong base such as n-butyllithium abstract the proton from the hydrazone (4) followed by the less acidic proton α to the hydrazone carbon (5), forming a carbanion. The carbanion then undergoes. an elimination reaction producing a carbon–carbon double bond and ejecting the tosyl anion, forming a diazonium anion (6).
Luche reduction is the selective organic reduction of α,β-unsaturated ketones to allylic alcohols. [ 1 ] [ 2 ] [ 3 ] The active reductant is described as "cerium borohydride", which is generated in situ from NaBH 4 and CeCl 3 (H 2 O) 7 .
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 ...
Diphenylmethanol may be prepared by a Grignard reaction between phenylmagnesium bromide and benzaldehyde [citation needed]. An alternative method involves reducing benzophenone with sodium borohydride or with zinc dust or with sodium amalgam and water.