I want to do a reaction where aldehyde has to react with carbanion.
I want to use Sodium hydride as base to create carbanion and aluminium chloride to activate aldehyde for nucleophilic substitution/addition.
Is it Ok?
Dear Billa,
Aluminium chloride reacts with calcium and magnesium hydrides in tetrahydrofuran forming tetrahydroaluminates. It might behave the same way with sodium hydride to some extent.
Hoping this will be helpful.
Dear Rafik sir,
Thank you very much for your time.
First I am generating the carbanion using Sodium hydride then adding aldehyde treated separately with aluminium chloride. Is it Ok..?
I am using DCM as solvent. And I am using excees sodium hydride and catalytic Aluminium chloride.
It is fine. However, instead of DCM you can use dry THF which is a better solvent for these reagents.
Good luck.
Dear Sir,
Thank you sir,
What is possibility of nucleophilic substitution in aldehydes? they are less reactive or inert? any reports for the nucleophilic substitution of aldehydes. especially with carbanion ( of oligomer where carbanion is stabilized by conjugation)
Dear Billa,
to the best of my knowledge, you can activate first the aldehyde using aluminium chloride ( about 0.5 equivalent) under inert condition and as a solvent, I suggest dry THF. To this rxn solution, you can add carefully the anion solution which also should be under dry conditions to ensure the activity of the generated anion.
GOOD LUCK.
Hi Billa,
The carbonyl group of aldehydes makes them very reactive as they can undergo nucleophilic addition ( not substitution) reactions.
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