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Related Concept Videos

Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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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...
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Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

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In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
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Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

2.7K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
2.7K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.9K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.1K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.1K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.1K
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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Updated: Nov 8, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Radical trifluoromethylation.

Haiwen Xiao1, Zhenzhen Zhang, Yewen Fang

  • 1School of Materials and Chemical Engineering, Ningbo University of Technology, 201 Fenghua Road, Ningbo 315211, China. fang@nbut.edu.cn.

Chemical Society Reviews
|April 23, 2021
PubMed
Summary
This summary is machine-generated.

This tutorial covers new methods for adding trifluoromethyl groups to carbon radicals. These advances are crucial for developing new pharmaceuticals, agrochemicals, and materials.

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Materials Science

Background:

  • The trifluoromethyl group is a key functional group in modern chemistry.
  • Its incorporation enhances the properties of pharmaceuticals, agrochemicals, and materials.

Purpose of the Study:

  • To review recent advancements in the trifluoromethylation of carbon-centered radical intermediates.
  • To provide a comprehensive overview of emerging synthetic strategies.

Main Methods:

  • Radical generation techniques.
  • Trifluoromethylating reagents and their mechanisms.
  • Catalytic and non-catalytic approaches.

Main Results:

  • Demonstration of diverse methods for efficient trifluoromethylation.
  • Highlighting the scope and limitations of current methodologies.
  • Discussion of the impact of these methods on synthetic efficiency.

Conclusions:

  • Trifluoromethylation of carbon radicals is a rapidly evolving field.
  • These advances offer powerful tools for molecular design.
  • Future directions include developing more sustainable and versatile methods.