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Radical Reactivity: Overview

Radical Reactivity: Overview

Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired molecule. These three...

Radical Formation: Addition

Radical Formation: Addition

Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an unpaired...

Radical Reactivity: Nucleophilic Radicals

Radical Reactivity: Nucleophilic Radicals

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For instance, consider...

Radical Reactivity: Intramolecular vs Intermolecular

Radical Reactivity: Intramolecular vs Intermolecular

Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak carbon–halogen...

Radical Formation: Overview

Radical Formation: Overview

A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the latter, also known...

Radical Reactivity: Steric Effects

Radical Reactivity: Steric Effects

The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic factors, steric factors also account...

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Related Experiment Video

Updated: Jun 2, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

Modern developments in aryl radical chemistry.

Gerald Pratsch¹, Markus R Heinrich

¹Pharmazeutische Chemie, Department für Chemie und Pharmazie der, Friedrich-Alexander-Universität Erlangen-Nürnberg, Germany.

Topics in Current Chemistry

|April 21, 2011

Summary

This summary is machine-generated.

This review highlights modern advances in aryl radical chemistry, focusing on established reactions like Meerwein and Pschorr, and their use in natural product synthesis. Emerging methods offer alternatives to traditional tin hydride reagents.

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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Aryl radical chemistry is crucial for synthesizing complex organic molecules.
Established reactions like Meerwein, Pschorr, and Gomberg-Bachmann are foundational.
Tin hydrides have been the primary reagents for aryl radical generation.

Purpose of the Study:

To review recent advancements in aryl radical chemistry.
To showcase novel applications in natural product synthesis.
To discuss emerging alternatives to tin hydride reagents.

Main Methods:

Review of modern developments in classical aryl radical reactions.
Exploration of new synthetic strategies utilizing aryl radicals.
Analysis of alternative methods for aryl radical generation.

Main Results:

Modernized versions of Meerwein, Pschorr, and Gomberg-Bachmann reactions are presented.
New applications of aryl radical chemistry in natural product synthesis are detailed.
Emerging, promising alternatives to tin hydrides for aryl radical generation are identified.

Conclusions:

Aryl radical chemistry continues to evolve with new synthetic applications.
Alternative methods to tin hydrides offer greener and more efficient radical generation.
The field shows significant promise for future synthetic endeavors.