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関連する概念動画

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.7K
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.
3.7K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.2K
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...
4.2K
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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関連する実験動画

Updated: Mar 19, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

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

Published on: March 20, 2017

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機能化されたサイクロペンテノンのC-H挿入方法

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
まとめ

この研究は,アルキノンから2-ブロモサイクロペント-2-エン-1-オンを合成するための新しい金触媒法を導入しています. このアプローチは,C-H挿入の限界を克服し,価値あるサイクロペンテノン構造への多用途な経路を提供します.

さらに関連する動画

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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関連する実験動画

Last Updated: Mar 19, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

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

Published on: March 20, 2017

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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科学分野:

  • 有機化学
  • カタリシス
  • 合成方法論

背景:

  • サイクロペンテノンは重要な合成構成要素です.
  • 直接的なC-H機能化は効率的な合成経路を提供します.
  • C-H挿入によるサイクロペンテノン合成の以前の方法は限られている.

研究 の 目的:

  • サイクロペンテノンの合成のための新しい金触媒方法を開発する.
  • 2-ブロモcyclopent-2-en-1-onesの効率的な構築を可能にするために.
  • ゴールド・ヴィニリデンの中間物質の反応性を調べるため

主な方法:

  • 金で触媒化された分子内C-H挿入反応.
  • アルキノン基板を使用しています.
  • 黄金ビニリデンの中間物質の生成は,新しい分子間戦略によって行われます.

主要な成果:

  • 広範囲にわたる2-ブロモcyclopent-2-en-1-onesの合成に成功した.
  • 合成的に望ましい diastereoselectivitiesを達成しました.
  • 黄金のヴィニリデンの 中間物質の形成を証明した.

結論:

  • 開発された金触媒方式は,機能化されたサイクロペンテノンの柔軟かつ効率的なアクセスを提供します.
  • 金のヴィニリデンの生成のための新しい分子間戦略は,合成の可能性を拡大します.
  • この研究は,有機合成における金ビニリデンの汎用的な反応性を探求するための道を開きます.