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[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.
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

6.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
6.6K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

8.0K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
8.0K
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
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

10.2K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
10.2K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

5.4K
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.
5.4K

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関連する実験動画

Updated: Apr 16, 2026

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
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Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

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Pd (II) -触媒化されたC-H機能化は,遠隔の弱調整機能群によって導かれます.

Gang Li1, Li Wan1, Guofu Zhang1

  • 1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society
|March 14, 2015
PubMed
まとめ

新しいオルソ-C ((sp ((2)) -Hオレフィネーションとアセトキシル化方法は,フェニラセチル誘導体の直接機能化を可能にします. これらの反応は,軽度な条件では弱い調整とリガンド加速度を利用し,合成の有用性を拡大します.

さらに関連する動画

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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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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関連する実験動画

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Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
06:26

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

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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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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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科学分野:

  • 有機化学 オーガニック・ケミストリー
  • カタリシス カタリシス カタリシス
  • 合成方法論 合成方法論

背景:

  • 直接的なC-H機能化は,効率的な合成経路を提供します.
  • 伝統的な方法は,しばしばグループを指導したり,厳しい条件を要求します.
  • ワインレブのアミド,エステル,ケトンは,汎用性の高い合成中間物質です.

研究 の 目的:

  • 新規のオーソ-C(sp(2)) -Hオレフィネーションおよびアセトキシル化反応を開発する.
  • これらの変換をフェニラセチル誘導体で追加的な指向群なしで達成するために.
  • これらの新しい方法論の範囲と限界を探求する.

主な方法:

  • パラジウム (((II) 触媒を用いて,バイデンテートアミノ酸リガンドを用いた.
  • 遠隔の弱い協調を用い,C-H活性化に直接作用する.
  • 軽度の反応条件におけるリガンド加速度の役割を調査する.

主要な成果:

  • フェニラセチルワインレブアミド,エステル,ケトンのオーソ-C ((sp ((2)) -Hオレフィン化とアセトキシル化が成功しました.
  • C-H結合と指向機能群の間のより長い距離に対する耐性を示した.
  • 水素シナモイルケトン,ワインレブアミド,ビフェニルワインレブアミドにおけるより遠隔のC-H結合の機能化が達成された.
  • 機械学的研究は,Pd (II) 誘導のC-H活性化におけるカルボニル群の役割を支持した.

結論:

  • 効率的で軽度のパラジウム触媒によるC-H機能化の方法を開発した.
  • この戦略は,事前に設置された指揮グループを必要としないようにしています.
  • この発見は,有機合成におけるワインレブアミドおよび関連する化合物の有用性を拡大する.