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Related Concept Videos

Radical Equations01:26

Radical Equations

60
Radical equations are mathematical expressions in which the variable is found within a radical, most commonly a square root or cube root. These equations frequently arise in science, engineering, and real-world measurements involving nonlinear relationships. To solve a radical equation, the standard procedure is to isolate the radical expression and then eliminate the radical by raising each side to a power equal to the index of the radical. This process may lead to extraneous...
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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.4K
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...
2.4K
Radical Formation: Overview01:03

Radical Formation: Overview

2.4K
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...
2.4K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.6K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
4.6K
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

4.2K
Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
4.2K
Radical Formation: Addition00:47

Radical Formation: Addition

2.0K
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...
2.0K

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Radical Smiles Rearrangement: An Update.

Ingrid Allart-Simon1, Stéphane Gérard2, Janos Sapi3

  • 1Institut de Chimie Mol&#233;culaire de Reims, UMR CNRS 7312, Universit&#233; de Reims-Champagne-Ardenne, Facult&#233; de Pharmacie, 51 rue Cognacq-Jay, F-51096 Reims Cedex, France. simoningrid@hotmail.fr.

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Summary

The Smiles rearrangement, a key tool in organic synthesis, has evolved with radical versions. These radical reactions, especially in domino processes, efficiently create complex, polyfunctionalized molecules.

Keywords:
Smiles rearrangementdomino reactionsheterocycleradical cascaderadical chemistry

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • The Smiles rearrangement is a fundamental reaction in organic synthesis.
  • Radical variants of the Smiles rearrangement have emerged as powerful synthetic tools.

Purpose of the Study:

  • To review recent advancements in the radical Smiles rearrangement.
  • To highlight the application of radical Smiles rearrangements in synthesizing complex molecules.

Main Methods:

  • Review of recent literature on radical Smiles rearrangements.
  • Focus on examples integrated into domino processes.

Main Results:

  • Demonstration of the synthetic utility of radical Smiles rearrangements.
  • Successful preparation of polyfunctionalized complex molecules using these methods.

Conclusions:

  • Radical Smiles rearrangements are highly effective synthetic strategies.
  • Domino processes involving radical Smiles rearrangements offer efficient routes to complex molecular architectures.