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Related Concept Videos

C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

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The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.4K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

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Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
1.6K
Mass Spectrometry: Cycloalkene Fragmentation00:54

Mass Spectrometry: Cycloalkene Fragmentation

1.5K
The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction.
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Radical Formation: Overview01:03

Radical Formation: Overview

1.9K
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...
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Asymmetric transformations via C-C bond cleavage.

Laetitia Souillart1, Evelyne Parker, Nicolai Cramer

  • 1Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, School of Basic Sciences, Ecole Polytechnic Fédérale de Lausanne, 1015, Lausanne, Switzerland.

Topics in Current Chemistry
|February 18, 2014
PubMed
Summary
This summary is machine-generated.

This review highlights advances in catalytic asymmetric transformations that cleave carbon-carbon bonds, creating novel organometallic species. Key developments include β-carbon eliminations and oxidative C-C bond insertions for versatile chemical synthesis.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Catalytic asymmetric transformations involving carbon-carbon (C-C) bond cleavage are increasingly important.
  • These reactions provide access to transient organometallic species through diverse pathways.
  • Significant progress has been made in expanding reaction scope and applicable substrates over the past decade.

Purpose of the Study:

  • To provide a comprehensive overview of recent developments in catalytic asymmetric C-C bond cleavage reactions.
  • To highlight the versatility and broad applicability of these transformations.
  • To discuss emerging strategies and key reaction classes.

Main Methods:

  • Focus on β-carbon eliminations of strained tert-alcohols and related reactions.
  • Discussion of asymmetric processes involving direct oxidative C-C bond insertion.
  • Analysis of reactions targeting acyl C-C bonds in ketones and C-CN bonds in nitriles.

Main Results:

  • β-carbon eliminations offer a versatile platform for various transformations.
  • Oxidative C-C bond insertion reactions demonstrate significant potential.
  • The field has seen considerable expansion in reactions and substrate scope.

Conclusions:

  • Catalytic asymmetric C-C bond cleavage represents a dynamic and evolving area of chemical synthesis.
  • These methods provide powerful tools for constructing complex molecules.
  • Future research promises further innovation in reaction design and application.