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Carbocations02:10

Carbocations

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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Valence Bond Theory

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Overview of Valence Bond Theory
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Bond Energies and Bond Lengths02:49

Bond Energies and Bond Lengths

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Stable molecules exist because covalent bonds hold the atoms together. The strength of a covalent bond is measured by the energy required to break it, that is, the energy necessary to separate the bonded atoms. Separating any pair of bonded atoms requires energy — the stronger a bond, the greater the energy required to break it.
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Bond Dissociation Energy and Activation Energy02:13

Bond Dissociation Energy and Activation Energy

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Bond energy is the energy required to break a bond homolytically. These values are usually expressed in units of kcal/mol or kJ/mol and are referred to as bond dissociation energies when given for specific bonds or average bond energies when indicated for a given type of bond over many compounds. Firstly, the bond dissociation energy for a single bond is weaker than that of a double bond, which in turn is weaker than that of a triple bond. Secondly, hydrogen forms relatively strong bonds with...
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Carbon Skeletons01:12

Carbon Skeletons

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Life on Earth is carbon-based, as all macromolecules that make up living organisms contain carbon atoms. All organic compounds have a carbon backbone. Each carbon atom is tetravalent and can bond with four other atoms, making it an extraordinarily flexible component of biological molecules. Because carbon’s valence electrons are stable, it rarely becomes an ion. As the carbon chain increases in length, structural modifications such as ring structures, double bonds, and branching side...
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Mass Spectrometry: Molecular Fragmentation Overview01:20

Mass Spectrometry: Molecular Fragmentation Overview

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The ionization of a molecule into a molecular ion inside the mass spectrometer causes instability in the molecule's structure due to the loss of an electron. This eventually leads to the fragmentation or breaking of some bonds in the molecule. The fragmentation occurs predominantly at specific bonds to yield relatively stable fragments.
One type of fragmentation pattern is the cleavage of a single bond in the molecular ion. The cleavage leads to a radical and a cation. The cleavage can...
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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When all C-C breaks LO-Ose.

Jeremy H Dworkin1, Brady W Dehnert1, Ohyun Kwon1

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569, USA.

Trends in Chemistry
|December 18, 2023
PubMed
Summary

Organic peroxides are key intermediates for new chemical reactions. Transition metals activate these compounds, enabling radical reactions that efficiently break and form carbon-carbon bonds, creating molecular complexity.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Radical Chemistry

Background:

  • Organic peroxides are increasingly utilized as versatile intermediates in modern synthetic chemistry.
  • The inherent reactivity of the peroxide O-O bond allows for facile activation by transition metals.
  • This activation initiates radical cascade processes, offering pathways for C-C bond cleavage and formation.

Purpose of the Study:

  • To review the historical development and synthesis of organic peroxides.
  • To highlight recent advancements in transition metal-mediated radical functionalization of C-C bonds using organic peroxides.
  • To provide essential safety considerations for handling organic peroxides.

Main Methods:

  • Review of literature focusing on the synthesis and application of organic peroxides.

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  • Analysis of transition metal-catalyzed reactions involving organic peroxide reduction.
  • Compilation and discussion of 91 examples of radical functionalization reactions.

    • Main Results:

    • Demonstration of organic peroxides as effective precursors for radical generation.
    • Showcasing the utility of iron and copper catalysts in mediating these transformations.
    • Highlighting the successful application of 91 distinct radical functionalization reactions for C-C bond manipulation.

    Conclusions:

    • Transition metal-mediated reduction of organic peroxides is a powerful strategy for C-C bond functionalization.
    • This methodology allows for the rapid construction of complex molecules through radical coupling.
    • Safe laboratory practices are crucial when working with organic peroxides.