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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: 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 Autoxidation01:20

Radical Autoxidation

3.1K
The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Radical Formation: Overview01:03

Radical Formation: Overview

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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 Formation: Homolysis00:54

Radical Formation: Homolysis

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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.
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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...
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An Organoborate Monoxide Radical.

Shuchang Li1, Gan Xu1, Yong Luo2

  • 1Department of Chemistry, State Key Laboratory of Marine Pollution, City University of Hong Kong, Kowloon Tong, 999077, Hong Kong SAR, P. R. China.

Journal of the American Chemical Society
|January 21, 2026
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Summary
This summary is machine-generated.

Researchers synthesized a stable organic boron monoxide radical, an oxygen-centered species stabilized by a boryl group. This novel radical exhibits unique reactivity and catalytic potential in coupling reactions.

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Area of Science:

  • Organometallic Chemistry
  • Radical Chemistry

Background:

  • Boron monoxide radicals were previously only observed as short-lived intermediates under matrix isolation.
  • Stable organic boron monoxide radicals have not been previously synthesized or characterized.

Purpose of the Study:

  • To synthesize and characterize a stable organic boron monoxide radical.
  • To investigate the stabilization and reactivity of this novel radical species.

Main Methods:

  • Reaction of a diboron(6) dianion with nitric oxide (NO).
  • Characterization using electron paramagnetic resonance (EPR) spectroscopy and single-crystal X-ray diffraction.
  • Stability studies under various conditions (argon, heating, UV light).

Main Results:

  • Successful synthesis and characterization of a stable, oxygen-centered organic boron monoxide radical.
  • The radical is stabilized by a triaryl-substituted boryl group and a K cation, showing stability at room temperature.
  • Demonstrated mimicry of transition-metal complexes in mediating NO coupling to form a boryl hyponitrite derivative.
  • Exhibited catalytic potential in tin-tin coupling reactions.

Conclusions:

  • A stable organic boron monoxide radical has been synthesized, expanding the known chemistry of boron monoxide.
  • This radical displays unique stability and reactivity, including potential catalytic applications.
  • The findings open new avenues for exploring boron-based radical chemistry and catalysis.