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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
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...
2.1K
Radical Formation: Overview01:03

Radical Formation: Overview

2.1K
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...
2.1K
Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
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...
1.7K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

1.7K
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...
1.7K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

1.9K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
1.9K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

3.5K
A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
3.5K

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Related Experiment Video

Updated: Jun 17, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

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Electrochemical radical cation aza-Wacker cyclizations.

Sota Adachi1, Yohei Okada1

  • 1Department of Applied Biological Science, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan.

Beilstein Journal of Organic Chemistry
|August 13, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces electrochemical radical cation aza-Wacker cyclizations, a novel method for generating reactive intermediates from stable compounds. These reactions offer new pathways for complex bond formation, advancing synthetic chemistry.

Keywords:
alkeneaza-Wacker cyclizationelectrochemistryradical cationsulfonamide

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Reaction Mechanisms

Background:

  • Single-electron oxidation generates radical cations, versatile intermediates in chemical synthesis.
  • Understanding the mechanisms of radical cation-mediated reactions is crucial for developing new synthetic methodologies.
  • Aza-Wacker cyclizations are important for forming nitrogen-containing heterocycles.

Purpose of the Study:

  • To report novel electrochemical radical cation aza-Wacker cyclizations.
  • To investigate the generation and reactivity of radical cations from alkenes under acidic conditions.
  • To elucidate the reaction mechanisms involved in these cyclizations.

Main Methods:

  • Electrochemical oxidation of bench-stable substrates.
  • Generation of radical cations via single-electron transfer.
  • Acid-catalyzed cyclization reactions.

Main Results:

  • Successful implementation of electrochemical radical cation aza-Wacker cyclizations.
  • Demonstration of unique reactivity of radical cation intermediates.
  • Insights into the mechanistic pathways of these complex transformations.

Conclusions:

  • Electrochemical generation of radical cations provides a powerful tool for aza-Wacker cyclizations.
  • This methodology expands the scope of radical cation chemistry in organic synthesis.
  • Further mechanistic studies are warranted to fully understand these intricate reactions.