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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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 low‐energy SOMO, which interacts...
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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...
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Radical Formation: Addition00:47

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: Steric Effects01:10

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...
Radical Reactivity: Nucleophilic Radicals01:16

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...

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Related Experiment Video

Updated: Jun 10, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

A crystalline phosphinyl radical cation.

Olivier Back1, Mehmet Ali Celik, Gernot Frenking

  • 1UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, California 92521-0403, USA.

Journal of the American Chemical Society
|July 29, 2010
PubMed
Summary
This summary is machine-generated.

Researchers created a stable phosphorus-centered radical cation from a phosphaalkene. This unique species, stable in solution and solid states, was characterized using X-ray diffraction, offering insights into phosphorus radical chemistry.

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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
12:06

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

Published on: October 19, 2017

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Last Updated: Jun 10, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
12:06

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

Published on: October 19, 2017

Area of Science:

  • Organophosphorus Chemistry
  • Radical Chemistry
  • Carbene Chemistry

Background:

  • Phosphaalkenes are unsaturated compounds containing a phosphorus-carbon double bond.
  • Cyclic (alkyl)(amino)carbenes are versatile ligands and precursors in organometallic chemistry.
  • Stable radical cations are valuable intermediates in chemical synthesis and mechanistic studies.

Purpose of the Study:

  • To synthesize and characterize a novel, stable phosphorus-centered radical cation.
  • To investigate the electronic structure and stability of the radical cation species.
  • To explore the potential of phosphaalkenes as precursors for stable radical species.

Main Methods:

  • One-electron oxidation of a phosphaalkene precursor.
  • Isolation and characterization of the resulting radical cation in solution and solid states.
  • Single-crystal X-ray diffraction analysis to determine molecular structure.

Main Results:

  • A readily available phosphaalkene was successfully oxidized to a stable phosphorus-centered radical cation.
  • The radical cation exhibited indefinite stability in both solution and solid states.
  • X-ray diffraction confirmed the structure of the stable radical cation, revealing its electronic properties.

Conclusions:

  • The study demonstrates the feasibility of generating indefinitely stable phosphorus-centered radical cations from phosphaalkenes.
  • The characterized species can be viewed as a phosphinyl radical with a cationic substituent or a carbene-stabilized phospheniumyl radical.
  • This work expands the understanding of reactive phosphorus intermediates and their stabilization.