Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.2K
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...
2.2K
Radical Formation: Addition00:47

Radical Formation: Addition

1.8K
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...
1.8K
Radical Formation: Overview01:03

Radical Formation: Overview

2.2K
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...
2.2K
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

3.6K
The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
3.6K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

3.7K
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.
3.7K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

3.6K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.6K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Dearomative [2 + 2] photocycloaddition to difluoro bicyclo[2.1.1]hexane bioisosteres.

Chemical science·2026
Same author

Combined All-trans Retinoic Acid and Rosiglitazone Alleviates Scleroderma Fibrosis by Suppressing the STAT3/Th17 Axis.

In vivo (Athens, Greece)·2026
Same author

Eosinophil count trajectories are associated with the prognosis of acute myocardial infarction patients: Insights from ICU data analysis.

PloS one·2026
Same author

Enantioselective Vinyl Radical Addition to Aldehydes via Dual Chromium Catalysis.

Angewandte Chemie (International ed. in English)·2026
Same author

Recent advances in photochemical rearrangements involving diradicals.

Chemical Society reviews·2026
Same author

Unexpected Chemoselectivity in Radical Aryl Translocation via Photosensitization.

Journal of the American Chemical Society·2026
Same journal

Machine-Learning-Enabled Rapid Evolution of Photoenzymes for the Asymmetric Synthesis of gem-Difluorophosphonates.

Angewandte Chemie (International ed. in English)·2026
Same journal

Sequential H<sub>2</sub>S-Triggered Redox Relay Nanoprobes for Self-Sustained Chem-Illuminating Cascade Photodynamic Therapy.

Angewandte Chemie (International ed. in English)·2026
Same journal

Quantitative Active Hydrogen Modulation via Mastering Interfacial Water Over Single Rare Earth Atom on Copper for NO<sub>3</sub> <sup>-</sup>-to-NH<sub>3</sub> Electroreduction.

Angewandte Chemie (International ed. in English)·2026
Same journal

Unveiling the Role of Hydroxyls on Catalyst Surface in CO<sub>2</sub> Hydrogenation Reaction.

Angewandte Chemie (International ed. in English)·2026
Same journal

Strain-Release Pentafluorosulfanylation of Carbonyl-Containing Disubstituted Bicyclobutanes: A Fortuitous Path to SF<sub>5</sub>-Containing Oxa[2.1.1]bicyclohexanes.

Angewandte Chemie (International ed. in English)·2026
Same journal

Quantum Spin-1/2 Rings Built From [2]Triangulene Molecular Units.

Angewandte Chemie (International ed. in English)·2026
See all related articles

Related Experiment Video

Updated: Sep 7, 2025

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow
10:34

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow

Published on: April 24, 2014

10.9K

Radical Brook Rearrangements: Concept and Recent Developments.

Ying Zhang1, Jun-Jie Chen1, Huan-Ming Huang1

  • 1School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210, P. R. China.

Angewandte Chemie (International Ed. in English)
|June 21, 2022
PubMed
Summary
This summary is machine-generated.

The radical Brook rearrangement, though less explored than its ionic counterpart, is gaining traction in synthetic chemistry. Recent advances in photocatalysis and transition-metal catalysis are expanding its applications in complex molecule synthesis.

Keywords:
Brook RearrangementCross-Coupling ReactionsPhotoredox ChemistryRadicalsTransition-Metal Catalysis

More Related Videos

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.4K
Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

11.9K

Related Experiment Videos

Last Updated: Sep 7, 2025

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow
10:34

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow

Published on: April 24, 2014

10.9K
Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.4K
Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

11.9K

Area of Science:

  • Synthetic organic chemistry
  • Organometallic chemistry

Background:

  • The Brook rearrangement is a vital tool in synthetic chemistry, with applications spanning drug discovery to materials science.
  • The radical pathway of the Brook rearrangement remains underexplored due to challenges in generating alkoxyl radical intermediates.

Purpose of the Study:

  • To provide a comprehensive overview of the radical Brook rearrangement.
  • To highlight recent advancements in photocatalytic and transition-metal-catalyzed radical Brook rearrangements.

Main Methods:

  • Literature review of early developments and concepts.
  • Summary of recent photocatalytic reactions.
  • Analysis of transition-metal-catalyzed cross-coupling reactions.

Main Results:

  • Established the importance of the Brook rearrangement in various chemical fields.
  • Identified challenges in generating radical species for the rearrangement.
  • Showcased novel synthetic strategies utilizing radical Brook rearrangements.

Conclusions:

  • The radical Brook rearrangement is an emerging area with significant potential.
  • Photocatalysis and transition-metal catalysis are key enablers for radical Brook rearrangements.
  • Further research is encouraged to expand the scope and applications of this reaction.