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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
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

Radical Reactivity: Nucleophilic Radicals

2.1K
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: Addition00:47

Radical Formation: Addition

1.7K
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...
1.7K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

1.9K
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...
1.9K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

1.7K
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...
1.7K
Radical Formation: Overview01:03

Radical Formation: Overview

2.1K
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...
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Updated: Jun 12, 2025

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

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Radical-mediated click-clip reactions.

Jiantao Zhao1, Huacheng Yu1, Xingchen Jin1

  • 1Key Lab of Organic Optoelectronics & Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing 100084, China.

Science (New York, N.Y.)
|September 19, 2024
PubMed
Summary
This summary is machine-generated.

Researchers developed a reversible click reaction using sulfilimine bonds. This breakthrough allows for precise on-demand cleavage, enabling new applications in depolymerizable materials and modified biomolecules.

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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

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Last Updated: Jun 12, 2025

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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Polymer Chemistry

Background:

  • Click reactions offer efficient and selective molecular coupling but typically lack reversibility.
  • Reversible click reactions are highly desirable for dynamic molecular systems and on-demand transformations.
  • Developing strategies for reversible bond formation and cleavage is crucial for advanced synthesis.

Purpose of the Study:

  • To establish a novel reversible click reaction pair based on sulfilimine chemistry.
  • To demonstrate the precise and on-demand cleavage of the formed sulfilimine linkage.
  • To explore the utility of this click-clip sequence in complex molecular architectures.

Main Methods:

  • Oxidative sulfilimine bond formation between phenothiazines and amines using N-bromosuccinimide.
  • Photoreductive cleavage of the sulfilimine bromide linkage at 380 nanometers.
  • Application of the reversible reaction in synthesizing depolymerizable macromolecules and modifying aminosaccharides.

Main Results:

  • Rapid and quantitative coupling of phenothiazines and amines via oxidative sulfilimine formation.
  • High-yield, quantitative reversion of sulfilimine bromides to starting materials upon photoreduction.
  • Demonstrated selectivity and efficiency in complex systems, including depolymerizable polymers and aminosaccharides.

Conclusions:

  • A novel sulfilimine-based click-clip reaction pair has been successfully developed.
  • The protocol enables precise, on-demand cleavage, significantly expanding the versatility of click chemistry.
  • This reversible strategy holds promise for advanced materials science and chemical biology applications.