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Related Concept Videos

Radical Formation: Addition00:47

Radical Formation: Addition

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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.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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

Radical Reactivity: Overview

2.0K
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...
2.0K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.0K
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...
2.0K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

4.9K
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 N-bromosuccinimide...
4.9K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.8K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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σ-Bond insertion reactions of two strained diradicaloids.

Arismel Tena Meza1, Christina A Rivera1, Huiling Shao1

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

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|February 12, 2025
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Summary

A novel synthetic method creates bicyclo[2.1.1]hexane scaffolds, valuable for drug discovery. This approach utilizes strained cyclic allenes and bicyclo[1.1.0]butanes, leveraging inherent diradicaloid character for efficient synthesis under mild conditions.

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Area of Science:

  • Synthetic organic chemistry
  • Medicinal chemistry
  • Reaction methodology development

Background:

  • Developing new synthetic methods is crucial for discovering novel medicines.
  • Saturated arene bioisosteres are highly sought-after structural motifs in drug design.
  • These bioisosteres often impart favorable drug-like properties, making them an active area of research.

Purpose of the Study:

  • To report a new synthetic methodology for accessing the bicyclo[2.1.1]hexane scaffold.
  • To demonstrate a method utilizing mild conditions and a simple protocol.
  • To provide access to functionalized bicyclo[2.1.1]hexanes relevant for drug discovery.

Main Methods:

  • The methodology involves the coupling of transiently generated cyclic allenes and bicyclo[1.1.0]butanes.
  • These strained reactants possess significant strain energies, facilitating the reaction.
  • The reaction is proposed to proceed via a diradical pathway, initiated by the innate diradicaloid character of the reactants, not external stimuli.

Main Results:

  • A novel synthetic route to the bicyclo[2.1.1]hexane core structure was established.
  • The reaction proceeds under mild conditions with an operationally simple protocol.
  • The method successfully couples two highly strained fragments, cyclic allenes and bicyclo[1.1.0]butanes.

Conclusions:

  • The developed method provides valuable access to functionalized bicyclo[2.1.1]hexanes for drug discovery.
  • Geometric distortion in reactants can be strategically employed to enable unique reactivity, specifically diradicaloid pathways.
  • This work encourages further exploration and application of diradicaloid chemistry in synthetic strategies.