Decarboxylation

Organic Chemistry Decarboxylation:

• Decarboxylation is an organic reaction process.
• Metal salts, particularly copper compounds, facilitate decarboxylation reactions via metal carboxylate complexes.
• Decarboxylation of aryl carboxylates can produce aryl anions for cross-coupling reactions.
• Decarboxylation of alkanoic acids is typically slow, except for beta-keto acids, β,γ-unsaturated acids, and α-phenyl, α-nitro, and α-cyanoacids that undergo accelerated decarboxylation.

Named Decarboxylation Reactions:

• Barton decarboxylation, Kolbe electrolysis, Kochi reaction, and Hunsdiecker reaction are radical reactions.
• Krapcho decarboxylation is a related reaction of an ester.
• Ketonic decarboxylation converts carboxylic acids to ketones and forms the basis of several named reactions.
• Decarboxylations are common in various organic transformations.

Hydrodecarboxylation:

• Involves converting carboxylic acids to hydrocarbons.
• Commonly associated with malonic ester synthesis and Knoevenagel condensations.
• Requires replacing the carboxyl group with a hydrogen atom through the conjugate base of the carboxyl group and an unsaturated receptor.
• Reactions with concentrated hydrochloric acid may involve initial addition of water and a proton.

Biochemical Decarboxylation:

• Decarboxylations are prevalent in biological processes and often catalyzed by specific cofactors.
• Examples include the conversion of α-ketoglutarate to succinyl-CoA.
• Biological decarboxylations play crucial roles in metabolic pathways and are essential for various biochemical conversions.

Case Studies on Decarboxylation:

• Decarboxylation of Tetrahydrocannabinolic acid is crucial for the psychoactive effects of cannabis, where heating converts it to psychoactive Tetrahydrocannabinol.
• Decarboxylation kinetics of THCA vary with temperature.
• Ascorbic acid catalyzes benzene formation from benzoic acid in beverages.
• Cyclohexenone catalyzes the decarboxylation of amino acids, yielding by-products.

Decarboxylation Data Sources