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関連する概念動画

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
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.
3.8K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.2K
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.
5.2K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.9K
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.
2.9K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.3K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
2.3K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

14.4K
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.
14.4K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.4K
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...
4.4K

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関連する実験動画

Updated: Apr 12, 2026

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

4.1K

テトラメチレンエタンの同値: 連続サイクロアディションの再帰反応剤

Paul A Wender1, Matthew S Jeffreys1, Andrew G Raub1

  • 1Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305-5080, United States.

Journal of the American Chemical Society
|May 12, 2015
PubMed
まとめ

研究者らは,連続的な [4 + 2] サイクロアディションを可能にする新しい反応剤を開発し,複雑な分子を効率的に構築しました. この発見は,医薬品や材料などの貴重な化合物を合成するための段階的な経済的なアプローチを提供します.

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • 合成化学 合成化学とは
  • カタリシス カタリシス カタリシス

背景:

  • 構造的複雑性を効率的に達成するには,各段階ごとに複数の結合を形成する反応が必要です.
  • ディエルス・アルダーと金属触媒によるサイクル添加は強力ですが,しばしば連続的な操作が必要です.
  • 単一の操作で複雑性の生成を増幅する反応剤が必要である.

研究 の 目的:

  • 再帰的なサイクル添加を行うことができる新種の反応剤を導入する.
  • 複雑なカーボおよびヘテロバイサイクルの構造を合成する際にこれらの反応剤の有用性を実証する.
  • この方法論を新しいソルバトクロミックフッ素酸化物の合成に適用する.

主な方法:

  • オレフィンメタテシスによる親再帰反応剤である2,3-ジメチレン-4-トリメチルシリルブタン-1-オール (DMTB) の合成.
  • 連続的なダイエルス・アルダーと金属触媒による [4 + 2]サイクル添加でDMTBを使用する.
  • ヴィニロログスなピーターソン除去を誘発して,第2回サイクル添加のためにダインを再生する.

主要な成果:

  • 開発された反応剤は,単一の触媒カスケードでバック・トゥ・バック [4 + 2]サイクル添加を容易にします.

さらに関連する動画

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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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

9.1K

関連する実験動画

Last Updated: Apr 12, 2026

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

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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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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

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  • この多成分反応は,効率的に多様なカーボおよびヘテロバイサイクルの構成要素を生成します.
  • ソルバトクロム性フッ素ホルモン6-DMAの3段階の合成が成功しました.

    • 結論:

    • 新しい再帰的反応剤は,有機合成における迅速な複雑性生成のための強力な戦略を提供します.
    • このアプローチは,貴重な分子を合成する段階,時間,コスト,廃棄物の節約を提供します.
    • この方法論は,天然製品,治療薬,イメージング剤,および材料の作成に適用できます.