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Related Concept Videos

Radical Autoxidation01:20

Radical Autoxidation

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...
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy radical...
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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 molecule. These three...
Radical Formation: Elimination00:51

Radical Formation: Elimination

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 to...

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Updated: Jun 17, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Organic transformations involving hydroxyl radicals.

Jie-Xi Guo1, Yi-Bin Zhang1, Wenhao Bao1

  • 1School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, 315211, China. weiwenting@nbu.edu.cn.

Chemical Communications (Cambridge, England)
|June 16, 2026
PubMed
Summary
This summary is machine-generated.

Hydroxyl radicals enable precise organic synthesis by functionalizing molecules. Innovations in their generation address challenges in byproduct control and harsh conditions, advancing sustainable chemistry.

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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations
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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Monitoring Equilibrium Changes in RNA Structure by 'Peroxidative' and 'Oxidative' Hydroxyl Radical Footprinting

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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations
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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Published on: January 4, 2018

Area of Science:

  • Organic Chemistry
  • Sustainable Chemistry
  • Reaction Mechanisms

Background:

  • Hydroxyl radical reactions are vital for functional group introduction and molecular reconstruction in organic synthesis.
  • Traditional hydroxyl radical generation methods face challenges due to harsh conditions and poor byproduct control, hindering sustainable development.
  • Recent innovations in hydroxyl radical generation strategies offer new avenues for precise molecular construction.

Purpose of the Study:

  • To systematically review advancements in hydroxyl radical generation strategies for organic transformations.
  • To analyze the generation pathways, mechanisms, and experimental verification of hydroxyl radicals.
  • To evaluate the performance, application scopes, and challenges of various hydroxyl radical generation approaches.

Main Methods:

  • Classification of organic transformation products based on hydroxyl radical reservoirs (alcohols, phenols, ketones, carboxylic acids, sulfonyl compounds).
  • In-depth analysis of hydroxyl radical generation pathways and reaction mechanisms.
  • Review of experimental verification methods for hydroxyl radical reactions.

Main Results:

  • Hydroxyl radicals exhibit excellent functional group compatibility and C-H bond activation, promoting C-O bond formation.
  • Diverse organic products, including alcohols, phenols, ketones, carboxylic acids, and sulfonyl compounds, can be synthesized.
  • Various generation approaches show distinct performance characteristics and application scopes.

Conclusions:

  • Innovations in hydroxyl radical generation are crucial for sustainable organic synthesis and precise molecular construction.
  • Understanding generation pathways and mechanisms guides reaction design and process optimization.
  • This review provides theoretical guidance for future research in drug development, materials science, and green chemistry.