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

2.5K
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...
2.5K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.3K
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...
2.3K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.3K
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.
Along with electronic...
2.3K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.8K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
4.8K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.1K
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...
2.1K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.5K
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...
2.5K

You might also read

Related Articles

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

Sort by
Same author

Harnessing the β-Silicon Effect for Radical Cyclopolymerization: Direct Access to Si-Containing Cyclic Olefin Polymers.

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

The translational roles of circular RNAs in cancers and their underlying molecular mechanisms.

Medical oncology (Northwood, London, England)·2026
Same author

Diverse radical transformations of allenic C(sp)-C(sp<sup>2</sup>) and C(sp<sup>3</sup>)-C(sp<sup>2</sup>) bonds enabled by silyl substitution.

Nature communications·2026
Same author

Integrated multi-omics profiling of treatment-naive cervix uteri premalignant lesions and cervical squamous cell carcinoma reveals ecosystem and drivers underlying cervical cancer progression.

Cell death & disease·2026
Same author

Protein-Based Nutrition for Chronic Wounds: A Clinician's Guide to Patient Selection, Dosing, Monitoring, and Outcomes.

Advances in wound care·2026
Same author

The CD4/CD8 ratio as an immune phenotype improves risk stratification for sepsis-associated acute kidney injury: A single-center, multi-ICU Chinese cohort study.

Journal of critical care·2026

Related Experiment Video

Updated: Dec 13, 2025

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

20.6K

Radical-Mediated Remote Functional Group Migration.

Xinxin Wu1, Chen Zhu1

  • 1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China.

Accounts of Chemical Research
|July 25, 2020
PubMed
Summary
This summary is machine-generated.

This study introduces functional group migration (FGM) and dock-migration strategies for efficiently difunctionalizing unactivated alkenes and remote C-H bonds. These methods enable novel radical-mediated transformations, expanding synthetic capabilities in organic chemistry.

More Related Videos

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

12.2K
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.4K

Related Experiment Videos

Last Updated: Dec 13, 2025

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

20.6K
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

12.2K
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.4K

Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Radical Chemistry

Background:

  • Radical difunctionalization of alkenes is crucial but typically requires activated substrates.
  • Unactivated alkenes, like aliphatic ones, present a significant synthetic challenge.
  • Existing methods rely on proximal groups to stabilize radical intermediates.

Purpose of the Study:

  • To develop novel strategies for the radical difunctionalization of unactivated alkenes.
  • To enable the functionalization of remote, unactivated C-H bonds.
  • To expand the scope and efficiency of alkene transformations.

Main Methods:

  • Intramolecular distal functional group migration (FGM) for unactivated alkenes.
  • Development of a 'dock-migration' strategy for intermolecular difunctionalization using sulfone-based reagents.
  • Application of FGM for radical-mediated functionalization of remote C(sp3)-H bonds.

Main Results:

  • Successful difunctionalization of unactivated alkenes via FGM with various functional groups.
  • Broadened scope of alkenes (activated and unactivated) using the dock-migration approach, achieving fluoroalkylheteroarylation, fluoroalkylalkynylation, and alkylation.
  • Demonstrated remote C(sp3)-H heteroarylation, cyanation, and vinylation using FGM strategies.

Conclusions:

  • FGM and dock-migration are powerful tools for overcoming limitations in alkene and C-H bond functionalization.
  • These methods provide access to complex molecules through efficient radical-mediated pathways.
  • The developed strategies significantly advance the field of synthetic organic chemistry.