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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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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...
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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using...
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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.
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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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Radical functionalization of allenes.

Rongnan Yi1, Qiang Li1,2, Long-Yong Xie3

  • 1Key Laboratory of Food & Environment & Drug Monitoring and Testing of Universities in Hunan Province, Hunan Police Academy, Changsha 410138, China.

Chemical Communications (Cambridge, England)
|April 7, 2025
PubMed
Summary
This summary is machine-generated.

This review highlights recent advances in radical functionalization of allenes, a reactive class of compounds. It covers new methods for synthesizing complex molecules, including drugs and natural products.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Allenes are highly reactive due to their lower stability compared to alkenes and alkynes.
  • Recent progress in radical functionalization has spurred new synthetic applications for allenes.
  • A comprehensive summary of these advancements has been lacking.

Purpose of the Study:

  • To systematically review recent advancements in the radical functionalization of allenes.
  • To cover difunctionalization and trifunctionalization of allene carbon atoms and C-Y bond functionalization.
  • To categorize studies based on radical types and discuss reaction mechanisms.

Main Methods:

  • Literature review of radical functionalization of allenes from the past five years.
  • Categorization of reactions by radical type (C-, N-, O-, S-, Se-centered).
  • Analysis of difunctionalization, trifunctionalization, and C-Y bond functionalization strategies.

Main Results:

  • Significant progress in radical difunctionalization and trifunctionalization of allenes.
  • Successful functionalization of C-H and C-Br bonds in allenes.
  • Diverse applications demonstrated in the synthesis of functionalized molecules.

Conclusions:

  • Radical functionalization of allenes has emerged as a powerful tool in organic synthesis.
  • This review provides a valuable resource for researchers in the field.
  • Future research can build upon these advancements for novel molecule synthesis.