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Related Concept Videos

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 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 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 Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy between bonds broken and bonds...
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...
Radical Reactivity: Concentration Effects01:20

Radical Reactivity: Concentration Effects

In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...

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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations
13:09

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

Published on: January 4, 2018

Radical carbonylations using a continuous microflow system.

Takahide Fukuyama1, Md Taifur Rahman, Naoya Kamata

  • 1Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.

Beilstein Journal of Organic Chemistry
|September 25, 2009
PubMed
Summary
This summary is machine-generated.

Radical carbonylation of alkyl halides in a microflow reactor yielded high amounts of carbonylated products. This study demonstrates efficient formylation, cyclization, and coupling reactions using common radical mediators.

Keywords:
V-65continuous flow systemmicroreactorradical carbonylationradical mediator

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Real-time Monitoring of Reactions Performed Using Continuous-flow Processing: The Preparation of 3-Acetylcoumarin as an Example
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Real-time Monitoring of Reactions Performed Using Continuous-flow Processing: The Preparation of 3-Acetylcoumarin as an Example

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Area of Science:

  • Organic Chemistry
  • Flow Chemistry
  • Radical Reactions

Background:

  • Carbonylation reactions are crucial for synthesizing carbonyl compounds.
  • Microflow reactors offer enhanced control and safety for pressurized reactions.
  • Radical-mediated reactions provide versatile synthetic pathways.

Purpose of the Study:

  • To investigate radical-based carbonylation of alkyl halides in a microflow reactor.
  • To explore the efficiency of formylation, carbonylative cyclization, and three-component coupling reactions.
  • To evaluate the utility of tributyltin hydride and TTMSS as radical mediators.

Main Methods:

  • Utilized a microflow reactor system for pressurized carbon monoxide gas reactions.
  • Employed radical mediators such as tributyltin hydride (Bu3SnH) or tris(trimethylsilyl)silane (TTMSS).
  • Investigated various radical-based carbonylation reactions including formylation, cyclization, and coupling.

Main Results:

  • Achieved good to excellent yields for all investigated carbonylation reactions.
  • Demonstrated the effectiveness of the microflow reactor for handling pressurized CO gas.
  • Confirmed the utility of Bu3SnH and TTMSS as efficient radical mediators.

Conclusions:

  • Microflow reactor technology enables efficient and safe radical carbonylation of alkyl halides.
  • The developed methods provide access to diverse carbonylated products with high yields.
  • This approach offers a valuable tool for synthetic organic chemistry.