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Related Concept Videos

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

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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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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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2.1K
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.
2.1K
Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

2.0K
Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
2.0K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.2K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.2K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.0K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
3.8K

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Gold-Catalyzed Arylative Cope Rearrangement.

Bidisha Paroi1, Chayanika Pegu1, Manoj V Mane2

  • 1Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal-, 462 066, India.

Angewandte Chemie (International Ed. in English)
|May 21, 2024
PubMed
Summary

This study introduces a new gold-catalyzed arylative Cope rearrangement for 1,6-heptadienes, expanding the scope of this important synthetic reaction. The method utilizes a cyclization-induced [3,3]-rearrangement with redox catalysis for stereoselective synthesis.

Keywords:
Cope rearrangementcross-couplinggold catalysisredox catalysisπ-activation

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Cope rearrangements are vital for stereoselective structural reorganization.
  • Previous methods were limited to parent 1,5-hexadienes.

Purpose of the Study:

  • To develop a novel gold-catalyzed arylative Cope rearrangement for 1,6-heptadienes.
  • To expand the substrate scope and applicability of Cope rearrangements.

Main Methods:

  • Gold-catalyzed arylative Cope rearrangement.
  • Cyclization-induced [3,3]-rearrangement.
  • Ligand-enabled gold redox catalysis.

Main Results:

  • Successfully achieved the gold-catalyzed arylative Cope rearrangement of 1,6-heptadienes.
  • Demonstrated a novel cyclization-induced [3,3]-rearrangement pathway.
  • Established the utility of ligand-enabled gold redox catalysis in this transformation.

Conclusions:

  • The developed method broadens the synthetic utility of Cope rearrangements.
  • Mechanistic studies provide insights into the reaction pathway.
  • This work offers a new tool for stereoselective synthesis.