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相关概念视频

[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.
Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors01:31

Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors

The Diels–Alder reaction is thermally reversible, meaning that the reaction reverts to the starting diene and dienophile under suitable temperatures. The forward reaction gives a cyclohexene derivative and is favored at low to medium temperatures. The reverse process, also called retro-Diels–Alder reaction, is a ring-opening process favored at high temperatures.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction.
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends on...

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相关实验视频

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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

异分子反应固体自我组装中的电荷转移力:成功设计了独特的 (单晶到单晶) Diels-Alder 循环添加.

J H Kim1, S V Lindeman, J K Kochi

  • 1Department of Chemistry, University of Houston, Houston, Texas 77204-5641, USA.

Journal of the American Chemical Society
|July 18, 2001
PubMed
概括
此摘要是机器生成的。

电子捐赠者/接受者相互作用使能产生反应性晶体. 这些晶体经历立体选择性迪尔斯-阿尔德反应,产生具有受控晶体结构的独特添加物.

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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科学领域:

  • 晶体学 晶体学是指结晶学.
  • 有机化学 有机化学
  • 材料科学 材料科学 材料科学

背景情况:

  • 电子捐赠者/接受器 (EDA) 相互作用是工程反应晶体的关键.
  • 在特定的捐赠者和接受者之间可以形成电荷转移pi复合体.

研究的目的:

  • 使用EDA相互作用研究异分子晶体的形成.
  • 探索这些晶体内的自发,立体选择性迪尔斯-阿尔德循环添加.
  • 为了分析地形化学转化和由此产生的引晶体结构.

主要方法:

  • 在bis ((alkylimino) -1,4-dithiin受体和炭素捐赠体之间形成电荷转移pi复合体.
  • 单晶X射线晶体学用于结构监测.
  • 核磁共振光谱用于对地形化学反应的动力分析.

主要成果:

  • 形成了异分子 (1:1) 晶体固体,经历了自发的 [2 + 4] 迪尔斯-阿尔德循环添加.
  • 灵活的1,4-迪提因部分促进了同质的拓化学转换,最小的晶格扭曲.
  • 通过反热力学方法产生了迪尔斯-阿尔德 adduct 的独特的单晶相.
  • 反应在没有晶体分解的情况下进行了高转换,允许持续监测.

结论:

  • 这项研究展示了通过EDA相互作用设计反应晶体的多功能方法.
  • 单晶中均的拓化学反应可以精确控制引物结构和包装.
  • 由此产生的"人工"晶体是稳定的,展示了材料合成的新途径.