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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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When cyclopropenes meet gold catalysts.

Frédéric Miege1, Christophe Meyer, Janine Cossy

  • 1Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS (UMR 7084), 10 rue Vauquelin 75231 Paris Cedex 05, France.

Beilstein Journal of Organic Chemistry
|August 2, 2011
PubMed
Summary

Cyclopropenes are versatile substrates in gold catalysis, enabling diverse reactions since 2008. This review highlights key contributions to this expanding field of study.

Keywords:
cyclopropenesgold carbenesgold catalysisgold-stabilized allylic cationsring-opening

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Organic Chemistry

Background:

  • Gold catalysis has emerged as a powerful tool in organic synthesis.
  • Cyclopropenes, strained three-membered alkenes, offer unique reactivity.
  • The integration of cyclopropenes into gold catalysis began in 2008.

Purpose of the Study:

  • To review the diverse applications of cyclopropenes in gold-catalyzed reactions.
  • To summarize recent advancements in this rapidly developing research area.
  • To provide a comprehensive overview of cyclopropene utilization in gold catalysis.

Main Methods:

  • Literature review of published research on gold-catalyzed reactions involving cyclopropenes.
  • Analysis of reaction mechanisms and substrate scope.
  • Compilation of key synthetic transformations and methodologies.

Main Results:

  • Cyclopropenes serve as effective substrates in various gold-catalyzed transformations.
  • Gold catalysts facilitate unique reaction pathways with cyclopropenes, leading to complex molecular architectures.
  • Significant progress has been made in expanding the scope and efficiency of these reactions.

Conclusions:

  • Cyclopropenes are valuable and versatile substrates in gold catalysis.
  • The field of gold-catalyzed reactions with cyclopropenes continues to grow, offering exciting synthetic possibilities.
  • This review consolidates current knowledge and highlights future directions.