You may recall that NaBH4 is used for the reduction of aldehydes and ketones.
Nitriles are less reactive than aldehydes and ketones.That would lead to lower yields.For formation of bonds between nitrogen and sp2-hybridized carbons (e.g.If a molecule contains both an amine and a carbonyl, then it can cyclize to give a cyclic amine.Heres the mechanism for imine formation, in case youve forgotten.Its possible to use the familiar reducing agent sodium borohydride (NaBH4) for this process.Direct treatment of benzylamine with an alkylating agent (e.g.
The carbon atom of a carbonyl group is bonded to two other atoms in addition to the oxygen atom.
The toxicities of ketones and esters are similar to those of aldehydes in acidbase reaction: Ketoenol tautomerism, acid- and base-catalyzed between ketones (or aldehydes) and their enol forms, which contain a hydroxyl group directly attached to a doubly bonded carbon atom: carboxylic acid: Oxidation Aldehyde.
NaBH4 can be a perfectly acceptable reducing agent for reductive amination.
Otherwise they too polymerize.
An even better approach involves the use of the slightly weaker reducing agent sodium cyanoborohydride (NaBH3CN).
Aldehydes ketones.8 D nitriles.
Theres no need to isolate the intermediate imine (which tend to be somewhat unstable anyway the reduction can be performed in situ (i.e.Also important is the oxidation of alkyl side chains of aromatic rings by strong oxidizing idee cadeau pote 19 ans agents organic compound Organic compound, any of a large class of chemical compounds in which one or more atoms of carbon are covalently linked to atoms of other elements, most.This is a much more controlled manner of forming nitrogen-carbon bonds.Employing a ketone will result in a branched alkyl substituent on the amine.In practice, NaBH3CN is a little bit better than NaBH4.The use of hydrazine hydrate, H2NNH2 H2O, and a base such as potassium hydroxide, KOH, (the Wolff-Kishner reaction) or zinc-mercury, Zn(Hg and hydrochloric acid (the Clemmensen reaction) removes the oxygen entirely and gives a hydrocarbon (rcho RCH3).Examples of other common aldehydes include acetaldehyde, glutaraldehyde, and acrolein.One must resort to alternative techniques.Notes What about installing a phenyl group (see above)?Reduce the imine with a reductant such as sodium cyanoborohydride (NaBH3CN sodium borohydride (NaBH4 or sodium tri-acetoxyborohydride (NaBH(OAc)3) giving a new amine.
Reductive amination is extremely versatile and can be used to install a large variety of different alkyl groups on an amine.
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