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

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

12.1K
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.
12.1K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
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.
3.3K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.2K
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...
2.2K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.6K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
4.6K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

5.3K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.3K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.1K
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.
4.1K

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関連する実験動画

Updated: Jan 9, 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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ディエネ覆いカルベン:サイクル添加,共聚合,および触媒への経路

Mamak Bakhtiari1, Ludwig Zapf1, Tanja Kunz1

  • 1Department of Chemistry, University of Alberta, 11227 Saskatchewan Dr., Edmonton, Alberta T6G 2G2, Canada.

Journal of the American Chemical Society
|December 10, 2025
PubMed
まとめ
この要約は機械生成です。

新たに合成され,機能化された新型ダイーン覆いカルベン (DECC) が開発された. そのフォスフィニデン複合体は,サイクロアディション反応を可能にし,金活性化アルキン水分化前触媒として作用する天然ゴム型コポリマーを形成する.

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

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Last Updated: Jan 9, 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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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

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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

Published on: September 18, 2016

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科学分野:

  • 有機金属化学
  • キャタリシス
  • ポリマー科学

背景:

  • N-ヘテロサイクリックカルベン (NHCs) は,有機金属化学における多用途リガンドである.
  • 独特の電子特性を持つ新しいカルベン構造の開発は,触媒の進歩に不可欠です.
  • カーベンのドナー部位の機能化は,新しい反応性中間物質につながる.

研究 の 目的:

  • 新型ダイエネコープカルベン (DECC) の合成と特徴づけ
  • DECCとその機能化された誘導体の電子特性と反応性を調査する.
  • 合成された複合体やポリマーの触媒的応用を探求する.

主な方法:

  • NHCの前駆体による酸化/二重脱プロトン化によるDECCの合成
  • セレニウムとフォスフィニデンのリガンドによるDECCの機能化.
  • DECC,フォスフィニデン複合体,および光譜技術を用いた結果の共ポリマーの特徴化.
  • サイクロアディション反応とアニオンコポリメリゼーションの調査.
  • アルキン水分化のための前触媒としてのコポリマーの評価

主要な成果:

  • デイネ・キャプテッド・カルベン (DECC),IPrの合成に成功した.
  • 機能化されたDECCデリバティブにおける例外的なπ受容性の実証.
  • フォスフィニデン複合体は,サイクロオクチンとダイネ局所化 [4 + 2] サイクロアディションを受けた.
  • フォスフィニデンの複合体をイソプレンでアニオン共ポリマー化すると,天然ゴム型の共ポリマーが得られる.
  • 結果として得られたコポリマーには,アルキン水分化前触媒としての活性が示された.

結論:

  • 開発されたDECCスキャフォールドは,新しい反応性中間物質にアクセスするためのユニークなプラットフォームを提供します.
  • DECCから派生したフォスフィニデン複合体は,サイクロアディションとポリメリゼーションを含む多用途の反応性を示す.
  • その結果生じる天然ゴム型共ポリマーは,金触媒によるアルキンの水分化のための再生可能で活性な前触媒として有望である.