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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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.
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.0K
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.
5.0K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

13.6K
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.
13.6K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

16.9K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
16.9K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.8K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.8K

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Related Experiment Video

Updated: Mar 19, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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A C-H Insertion Approach to Functionalized Cyclopentenones.

Youliang Wang1, Maxence Zarca1, Liu-Zhu Gong2

  • 1Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93106, United States.

Journal of the American Chemical Society
|June 9, 2016
PubMed
Summary

This study introduces a novel gold-catalyzed method for synthesizing 2-bromocyclopent-2-en-1-ones from alkynones. This approach overcomes limitations in C-H insertion, offering a versatile route to valuable cyclopentenone structures.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Cyclopentenones are important synthetic building blocks.
  • Direct C-H functionalization offers an efficient synthetic route.
  • Previous methods for cyclopentenone synthesis via C-H insertion are limited.

Purpose of the Study:

  • To develop a novel gold-catalyzed method for cyclopentenone synthesis.
  • To enable the efficient construction of 2-bromocyclopent-2-en-1-ones.
  • To explore the reactivity of gold vinylidene intermediates.

Main Methods:

  • Gold-catalyzed intramolecular C-H insertion reaction.
  • Utilizing alkynone substrates.
  • Generation of gold vinylidene intermediates via a novel intermolecular strategy.

Main Results:

  • Successful synthesis of 2-bromocyclopent-2-en-1-ones with a broad scope.
  • Achieved synthetically desirable diastereoselectivities.
  • Demonstrated the formation of a key gold vinylidene intermediate.

Conclusions:

  • The developed gold-catalyzed method provides a flexible and efficient access to functionalized cyclopentenones.
  • The novel intermolecular strategy for gold vinylidene generation expands synthetic possibilities.
  • This work opens avenues for exploring the versatile reactivity of gold vinylidenes in organic synthesis.