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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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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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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: Nucleophilic Radicals01:16

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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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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.
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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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A Bottleable Imidazole-Based Radical as a Single Electron Transfer Reagent.

Arpan Das1, Jasimuddin Ahmed1, N M Rajendran1

  • 1Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, 741246, India.

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Researchers synthesized a novel imidazole-based radical, a versatile single electron transfer reagent. This radical facilitates various organic transformations, including aryl-halide bond activation and CO2 reduction, under mild conditions.

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Area of Science:

  • Organic Chemistry
  • Radical Chemistry
  • Catalysis

Background:

  • Imidazolium salts are precursors to N-heterocyclic carbenes.
  • Stable organic radicals are valuable reagents in electron transfer processes.
  • Development of new electron donors is crucial for sustainable chemistry.

Purpose of the Study:

  • To synthesize and characterize a novel imidazole-based radical.
  • To evaluate its potential as a single electron transfer reagent.
  • To explore its applications in organic transformations.

Main Methods:

  • Reduction of 1,3-bis(2,6-diisopropylphenyl)-2,4-diphenyl-1H-imidazol-3-ium chloride.
  • Characterization of the resulting imidazole-based radical.
  • Testing the radical's reactivity in single electron transfer reactions and catalytic transformations.

Main Results:

  • Formation of the first structurally characterized imidazole-based radical.
  • Demonstration of the radical as an effective single electron transfer reagent.
  • Successful application in aryl-halide bond activation, alkene hydrosilylation, and CO2 reduction.

Conclusions:

  • The novel imidazole-based radical is a stable and versatile electron donor.
  • It enables important organic transformations under ambient conditions.
  • This work expands the scope of radical chemistry in organic synthesis.