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Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

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Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.

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Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
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Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...

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Related Experiment Video

Updated: Oct 5, 2025

Light-driven Enzymatic Decarboxylation

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

Direct decarboxylative Giese reactions.

David M Kitcatt¹, Simon Nicolle², Ai-Lan Lee¹

¹Institute of Chemical Sciences, School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK. a.lee@hw.ac.uk.

Chemical Society Reviews

|January 31, 2022

Summary

This summary is machine-generated.

Carboxylic acids are sustainable precursors for generating carbon radicals. These radicals readily form carbon-carbon bonds via the Giese reaction, offering a greener approach in radical chemistry.

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

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Published on: April 4, 2014

Area of Science:

Organic Chemistry
Radical Chemistry

Background:

Growing demand for sustainable and mild synthetic methods.
Radical chemistry offers pathways to reactive intermediates.
Carboxylic acids are abundant, cost-effective, and sustainable radical precursors.

Purpose of the Study:

To review recent advancements in utilizing carboxylic acids as direct radical precursors.
To highlight their application in carbon-carbon bond formation via the Giese reaction.

Main Methods:

Direct use of carboxylic acids.
Radical decarboxylation process to generate carbon radicals.
1,4-Radical conjugate addition (Giese reaction) for C-C bond formation.

Main Results:

Carboxylic acids efficiently generate carbon radicals.
Extrusion of CO2 as a traceless byproduct.
Successful application in Giese reactions for C-C bond formation.

Conclusions:

Carboxylic acids are versatile and sustainable precursors for radical chemistry.
The Giese reaction provides an effective route for C-C bond formation using these precursors.
This approach aligns with the principles of green chemistry.