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Related Concept Videos

Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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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...
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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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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...
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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.6K
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...
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Radical Formation: Addition00:47

Radical Formation: Addition

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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...
2.1K
Radical Formation: Overview01:03

Radical Formation: Overview

2.6K
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...
2.6K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.3K
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...
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Related Experiment Video

Updated: Jan 3, 2026

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow
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Chemistry with Electrochemically Generated N-Centered Radicals.

Peng Xiong1, Hai-Chao Xu1

  • 1State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , P. R. China.

Accounts of Chemical Research
|November 28, 2019
PubMed
Summary
This summary is machine-generated.

This study introduces novel electrochemical methods for generating N-centered radicals from N-H bonds, enabling efficient synthesis of N-heterocycles. These electrocatalytic approaches offer sustainable alternatives to traditional methods, avoiding harsh reagents and promoting selective transformations.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Methodology

Background:

  • N-centered radicals are key intermediates for C-N bond formation.
  • Generating N-centered radicals from N-H bonds is challenging compared to N-heteroatom bonds.
  • Electrochemical methods offer a promising avenue for N-centered radical generation and utilization.

Purpose of the Study:

  • To develop and summarize electrochemical methods for generating and using N-centered radicals from N-H precursors.
  • To explore the synthetic applications of N-aryl amidyl, amidinyl, and iminyl radical intermediates.
  • To investigate the electrocatalytic conversion of oximes to iminoxyl radicals.

Main Methods:

  • Direct and indirect electrolysis for generating N-aryl amidyl, amidinyl, and iminyl radical cations from N-H compounds.
  • Electrocatalytic oxidation of oximes to iminoxyl radicals.
  • Utilizing generated radicals in cyclization and intramolecular aromatic substitution reactions.

Main Results:

  • Electrophilic amidyl radicals undergo exo-cyclization with alkenes/alkynes, forming C-centered radicals that lead to N-heterocycles.
  • Amidinyl radicals, iminyl radical cations, and iminoxyl radicals participate in intramolecular aromatic substitution to yield N-heteroaromatics.
  • Electrochemical reactions demonstrate high selectivity, controlled by electrode processes and simultaneous anodic/cathodic reactions, enabling dehydrogenative transformations without chemical oxidants.

Conclusions:

  • Electrochemical methods provide efficient and selective routes for synthesizing N-heterocycles and N-heteroaromatics from N-H precursors.
  • The described electrocatalytic strategies offer sustainable and mild alternatives, avoiding stoichiometric bases and harsh oxidants.
  • Tuning electrode materials and reaction conditions allows precise control over product outcomes, including N-heteroaromatics and their N-oxides.