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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...

Radicals: Electronic Structure and Geometry

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This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...

Radical Reactivity: Overview

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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...

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Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect to...

Radical Reactivity: Intramolecular vs Intermolecular

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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 Substitution: Allylic Bromination

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

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Related Experiment Video

Updated: Jun 22, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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A convergent radical-based route to biaryls.

Béatrice Quiclet-Sire¹, Guillaume Revol, Samir Z Zard

¹Laboratoire de Synthèse Organique, CNRS UMR 7652, Département de Chimie, Ecole Polytechnique, 91128 Palaiseau, France.

Organic Letters

|June 5, 2009

Summary

A new method synthesizes biaryl-3-carboxylate esters using radical 1,2-aryl migration. This process involves xanthate addition to olefins, followed by an aryl shift and microwave-assisted cyclization.

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Area of Science:

Organic Chemistry
Synthetic Methodology

Background:

Biaryl compounds are prevalent in pharmaceuticals and materials.
Efficient synthetic routes to substituted biaryl esters are highly sought after.

Purpose of the Study:

To develop a novel synthetic strategy for biaryl-3-carboxylate esters.
To utilize radical 1,2-aryl migration for constructing the biaryl core.

Main Methods:

Radical addition of xanthates to olefins.
1,2-aryl migration triggered by radical intermediates.
Microwave-assisted cyclization using 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU).

Main Results:

Successful synthesis of biaryl-3-carboxylate esters.
Demonstration of a radical-mediated 1,2-aryl migration.
Efficient conversion to the target biaryl structure under microwave irradiation.

Conclusions:

A novel and efficient route to biaryl-3-carboxylate esters has been established.
The developed method offers a valuable tool for accessing complex biaryl structures.
Radical 1,2-aryl migration provides a unique pathway in organic synthesis.