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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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Intermolecular forces (IMF) are electrostatic attractions arising from charge-charge interactions between molecules. The strength of the intermolecular force is influenced by the distance of separation between molecules. The forces significantly affect the interactions in solids and liquids, where the molecules are close together. In gases, IMFs become important only under high-pressure conditions (due to the proximity of gas molecules). Intermolecular forces dictate the physical properties of...
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Intramolecular Aldol Reaction01:18

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Intramolecular aldol reaction occurs in dicarbonyl compounds such as dialdehydes, diketones, and keto-aldehydes. The dicarbonyl compounds possess more than one nucleophilic ⍺ carbon for the base to deprotonate and form the enolates. For example, in symmetrical diketones, there are four ⍺ carbons. Hence, four types of enolates are possible when treated with a base. However, since the molecule is symmetrical, the enolates formed on either side of one carbonyl group are equivalent to those...
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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Radical Reactivity: Electrophilic Radicals01:02

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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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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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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...
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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
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E-Olefins through intramolecular radical relocation.

Ajoy Kapat1, Theresa Sperger1, Sinem Guven1

  • 1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany.

Science (New York, N.Y.)
|January 26, 2019
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Summary

A novel nickel-catalyzed reaction enables efficient synthesis of E-olefins via radical-based 1,3-hydrogen atom relocation. This cost-effective method offers precise control over stereochemistry, advancing olefin synthesis for various industries.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Stereochemically defined olefins are crucial building blocks in pharmaceuticals, materials, and petrochemicals.
  • Existing double-bond migration methods often rely on expensive precious metals, leading to issues like poor stereoselectivity and reversible reactions.

Purpose of the Study:

  • To develop a fundamentally different, cost-effective, and highly selective method for carbon-carbon double-bond migration.
  • To achieve precise control over E/Z stereochemistry in olefin synthesis using a non-precious metal catalyst.

Main Methods:

  • Utilizing a nickel (Ni)(I) catalyst for an intramolecular 1,3-hydrogen atom relocation.
  • Employing a radical-based approach that is reductant-free and atom-economical.
  • Conducting reactions at room temperature for 3 hours.

Main Results:

  • Successfully synthesized E-olefins with high stereoselectivity.
  • Demonstrated the ability to install E-olefins over extended molecular distances.
  • Achieved efficient double-bond migration using a non-precious metal catalyst.

Conclusions:

  • The developed nickel-catalyzed radical reaction offers a superior alternative to traditional precious-metal-based methods for olefin synthesis.
  • This approach provides a scalable, efficient, and stereoselective route to valuable E-olefins.
  • The methodology broadens the synthetic accessibility of stereochemically defined olefins for diverse industrial applications.