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

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

10.2K
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: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.1K
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...
4.1K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.9K
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.
3.9K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

6.1K
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...
6.1K
Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors01:31

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

5.0K
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.
5.0K

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The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
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Exo-Selective Diels-Alder Reactions.

Yuan-He Li1, Jia-Hua Chen1, Zhen Yang1,2,3

  • 1Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 27, 2024
PubMed
Summary
This summary is machine-generated.

This review explores exo-Diels-Alder reactions, detailing factors influencing selectivity beyond the typical endo rule. Strategies for controlling exo-Diels-Alder reactions are presented for predictable synthesis.

Keywords:
Diels–Alder reactionscatalysisexo-selectivitypericyclic reactionss-cis conformation

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Area of Science:

  • Organic Chemistry
  • Stereoselective Synthesis

Background:

  • The Diels-Alder reaction is a fundamental organic transformation for creating complex molecules.
  • The "endo rule" governs stereoselectivity but limits access to exo-adducts.

Purpose of the Study:

  • To review recent advancements in achieving exo-Diels-Alder reactions.
  • To elucidate factors controlling exo/endo selectivity.
  • To present strategies for designing predictable exo-Diels-Alder reactions.

Main Methods:

  • Analysis of recent literature examples of exo-Diels-Alder reactions.
  • Investigation of steric, electrostatic, and orbital interactions.
  • Exploration of thermodynamic influences on selectivity.
  • Review of strategies including bulky substituents, s-cis conformations, and control physics.

Main Results:

  • Identified key factors influencing exo/endo selectivity in Diels-Alder reactions.
  • Demonstrated strategies to override the endo rule and favor exo-products.
  • Highlighted the role of specific reaction conditions and molecular designs.

Conclusions:

  • Understanding and manipulating reaction parameters enables control over exo-Diels-Alder selectivity.
  • This knowledge facilitates the development of new diastereoselective catalysts.
  • Expands the synthetic utility of the Diels-Alder reaction for complex molecule synthesis.