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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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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...
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Free-energy diagrams, or reaction coordinate diagrams, are graphs showing the energy changes that occur during a chemical reaction. The reaction coordinate represented on the horizontal axis shows how far the reaction has progressed structurally. Positions along the x-axis close to the reactants have structures resembling the reactants, while positions close to the products resemble the products.  Peaks on the energy diagram represent stable structures with measurable lifetimes, while...
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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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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Kinetics describes the rate and path by which a reaction occurs. In contrast, thermodynamics deals with state functions and describes the properties, behavior, and components of a system. It is not concerned with the path taken by the process and cannot address the rate at which a reaction occurs. Although it does provide information about what can happen during a reaction process, it does not describe the detailed steps of what appears on an atomic or a molecular level. On the other hand,...
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Intermolecular reaction screening as a tool for reaction evaluation.

Karl D Collins1, Frank Glorius1

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Intermolecular screens offer a rapid and broad evaluation of new synthetic reactions, assessing functional group tolerance and stability. This method complements traditional substrate scope analysis for broader applicability in organic chemistry.

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Area of Science:

  • Synthetic organic chemistry
  • Methodology development
  • High-throughput screening

Background:

  • New synthetic methods are crucial for accessing novel structures and improving reaction efficiency, safety, and economics.
  • Evaluating reaction scope and limitations is essential for practical application in synthesis.
  • Traditional substrate scope analysis has limitations in comprehensively assessing functional group tolerance.

Purpose of the Study:

  • To highlight the benefits of comprehensive reaction evaluation using intermolecular screens.
  • To introduce and discuss a formal high-throughput intermolecular screening protocol.
  • To demonstrate the broad applicability and utility of intermolecular screens across diverse chemical reactions.

Main Methods:

  • Discussion of reaction evaluation criteria for target-oriented synthesis.
  • Introduction and comparison of intermolecular reaction screening with traditional substrate scope.
  • Development and application of a high-throughput intermolecular screening protocol.

Main Results:

  • Intermolecular screens provide a broader evaluation of functional group tolerance and stability compared to typical reaction scopes.
  • The developed high-throughput protocol enables rapid assessment of new chemical reactions.
  • Intermolecular screens have been successfully applied to diverse chemistries, including C-H functionalization, catalysis, and polymer science.

Conclusions:

  • Intermolecular screening is a valuable and practical tool for evaluating new synthetic methods.
  • This approach complements traditional methods and facilitates the broader application of new reactions.
  • The simplicity and versatility of intermolecular screens underscore their significant potential in synthetic organic chemistry.