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Related Concept Videos

Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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 low‐energy SOMO, which interacts...
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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 instance, consider...
Radical Formation: Addition00:47

Radical Formation: Addition

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 unpaired...
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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 carbon–halogen...
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

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...
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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Related Experiment Video

Updated: Jun 9, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Iodoform-Mediated Radical Iodinative Amidation Toward γ-Lactam.

Mengyan Gao1, Rui Yang1, Linyang Jiang1

  • 1School of Chemistry & Materials, Yangzhou University, Yangzhou, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 8, 2026
PubMed
Summary

This study introduces a new photochemical method using iodoform to create gamma-lactam derivatives. This visible light-driven process offers a simpler, metal-free alternative for synthesizing these important chemical structures.

Keywords:
5‐exo‐trig cyclizationamidyl radicaliodoformtransition metal‐freeγ‐lactam

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

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08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Synthetic Methodology

Background:

  • Gamma-lactam derivatives are important heterocyclic compounds with diverse biological activities.
  • Previous methods for synthesizing gamma-lactams often require harsh conditions or transition metal catalysts.
  • Developing efficient and sustainable synthetic routes to gamma-lactams remains a key challenge in organic chemistry.

Purpose of the Study:

  • To develop a novel visible light photochemical protocol for the synthesis of gamma-lactam derivatives.
  • To utilize iodoform as a readily available iodine source for radical generation.
  • To establish a metal-free and efficient method for iodinative amidation.

Main Methods:

  • Visible light irradiation was employed to initiate a radical cascade reaction.
  • Iodoform served as the iodine atom source through homolytic C-I bond cleavage.
  • Unsaturated carboxylic acid derived secondary amides were used as substrates.

Main Results:

  • The protocol successfully synthesized various gamma-lactam derivatives.
  • The reaction proceeded efficiently under mild, visible light conditions.
  • High functional group tolerance was observed, showcasing the robustness of the method.
  • The process avoided the need for any transition metal catalysts.

Conclusions:

  • A novel visible light photochemical radical iodinative amidation protocol has been established.
  • This method provides an efficient, metal-free, and sustainable route to gamma-lactam derivatives.
  • The protocol offers advantages over existing methods, including simplicity and broad substrate scope.