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

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

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.
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.

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Updated: Jul 3, 2026

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

レドックス交換可能なアルファサイクロデクストリン基 [2]ロタキサン.

Yan-Li Zhao1, William R Dichtel, Ali Trabolsi

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.

Journal of the American Chemical Society
|August 6, 2008
PubMed
まとめ
この要約は機械生成です。

アルファ-サイクロデクストリン環とリドックス活性テトラチアフルバレン系を特徴とする新しいビスタブルロタキサンが合成されました. アルファ-サイクロデクストリン環は,酸化還元刺激により,テトラチアフルワレンとトリアゾール単位の間を制御的に移動します.

さらに関連する動画

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
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The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

Published on: August 25, 2016

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

関連する実験動画

Last Updated: Jul 3, 2026

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
07:02

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

Published on: August 25, 2016

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

科学分野:

  • 超分子化学 超分子化学
  • 分子機械とは,分子機械のこと.
  • オーガニック・シンセシス オーガニック・シンセシス

背景:

  • ロタキサンは,ナノテクノロジーにおける潜在的な応用を持つ,機械的に相互に絡み合っている分子です.
  • 分子構成要素の動きを制御することは,機能的な分子装置の開発に不可欠です.
  • レドックス活性ユニットは,分子運動に対する外部制御のための経路を提供します.

研究 の 目的:

  • リドックス活性テトラチアフルバレン (TTF) ユニットとアルファ-サイクロデクストリン (alpha-CD) リングを組み込んだビスタブル [2]ロタキサンを合成する.
  • TTFとトリアゾール分子の間のアルファ-CD環の酸化還元誘導運動を解明する.
  • アルファ-CDリングの好ましい結合部位を定量的に,半定量的に決定する.

主な方法:

  • Cu ((I)) 触媒によるアジド-アルキンサイクル添加による合成.
  • 結合親和性研究のためのマイクロカロリメトリック定位.
  • レドックス駆動スイッチングのための電気化学実験 (サイクル電圧測定法).
  • 構造確認のためのスペクトロスコピクおよびカイロプティック測定.

主要な成果:

  • アルファ-サイクロデクストリンとTTFを含むダンベルを併用したビスタブル [2] ロタキサンの合成に成功した.
  • アルファ-サイクロデクストリンリングは,トリアゾールユニットよりも優先してTTFユニットと結合します.
  • レドックス誘発によるTTFの酸化により,アルファ-CD環がトリアゾールユニットに移動する.
  • 切り替えは,酸化されたTTF種を減少させると逆戻りします.

結論:

  • 合成されたビスタブル [2]ロタキサンは,リドックス刺激に基づいて制御可能で可逆的な分子スイッチングを示しています.
  • この研究は,アルファ-サイクロデキストリンのTTF単位への優先結合に関する定量的な証拠を提供します.
  • この研究は,酸化還元処理可能な分子機械とスイッチの開発に寄与しています.