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Related Concept Videos

Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
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...
1.7K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
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...
2.1K
Radical Formation: Elimination00:51

Radical Formation: Elimination

1.8K
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...
1.8K
Radical Formation: Overview01:03

Radical Formation: Overview

2.1K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
2.1K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

1.9K
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...
1.9K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.2K
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...
2.2K

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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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Radical annulation using a radical reagent as a two-carbon unit.

Boxiao Tang1, Yilin Liu1, Yan Lian1

  • 1Hunan Engineering Laboratory for Preparation Technology of Polyvinyl Alcohol (PVA) Fiber Material, Institute of Organic Synthesis, Huaihua University, Huaihua 418000, China. liuyilinhn@126.com.

Organic & Biomolecular Chemistry
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Summary

Radical annulation, a key synthetic method, efficiently builds cyclic compounds. Recent advances using two-carbon radical reagents expand molecular diversity and reaction possibilities in organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Radical annulation is a powerful strategy for constructing cyclic and polycyclic molecular frameworks.
  • This method offers efficiency through multi-bond-forming steps in a single procedure.

Purpose of the Study:

  • To review recent advancements in radical annulation reactions utilizing two-carbon radical reagents.
  • To highlight key reaction mechanisms and synthetic applications.

Main Methods:

  • Focus on radical annulation strategies involving two-carbon radical reagents.
  • Discussion of various cycloaddition modes: [2+2+2], [3+2], [4+2], and [5+2].
  • Emphasis on mechanistic insights into these radical processes.

Main Results:

  • Demonstration of expanded cyclic skeleton diversity through radical annulation.
  • Showcasing enhanced functionality of radical reagents in cyclization reactions.
  • Compilation of representative processes from the last decade.

Conclusions:

  • Recent radical annulation methods significantly broaden synthetic possibilities.
  • These studies offer valuable insights into novel reaction modes within radical chemistry.
  • The reviewed processes provide a foundation for future synthetic innovations.