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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 Formation: Elimination00:51

Radical Formation: Elimination

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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...
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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.6K
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: Overview01:11

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...
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Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

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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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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.3K
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...
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Transient N-Aziridinyl Radicals in Olefin Functionalization.

Promita Biswas1, David C Powers1

  • 1Department of Chemistry, Texas A&M University, 3255 TAMU, 580 Ross St, College Station, TX 77843.

Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry
|April 10, 2026
PubMed
Summary
This summary is machine-generated.

Researchers developed N-aziridinyl radicals for novel olefin hydroxyaziridination. This breakthrough introduces new synthetic pathways for aziridine chemistry, expanding access to complex molecules.

Keywords:
N-aminopyridinium saltsaziridinesnitrogen-centered radicalsolefin functionalization

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Aziridines, the smallest nitrogen heterocycles, are crucial for the biological activity of natural products and active pharmaceutical ingredients (APIs).
  • Traditional aziridine synthesis involves acyclic precursors via cycloaddition or intramolecular cyclization.
  • The direct introduction of intact aziridines is an uncommon synthetic disconnection.

Purpose of the Study:

  • To introduce N-aziridinyl radicals as novel synthetic intermediates.
  • To develop a new method for olefin hydroxyaziridination.
  • To explore new disconnections in aziridine chemistry.

Main Methods:

  • Generation of N-aziridinyl radicals via photoredox activation of N-pyridinium aziridine precursors.
  • Application of these radicals in hydroxyaziridination reactions with olefins.
  • Investigation of epoxide opening reactions with N-aziridine nucleophiles.

Main Results:

  • Successful generation and utilization of N-aziridinyl radicals.
  • Demonstration of novel olefin hydroxyaziridination.
  • Discovery of unprecedented epoxide opening reactions with N-aziridine nucleophiles.

Conclusions:

  • N-aziridinyl radicals represent a significant advancement in synthetic chemistry.
  • This work establishes new synthetic disconnections for aziridine chemistry.
  • The developed methodology broadens the scope of accessible aziridine-containing compounds.