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

[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 Reaction Forming Bridged Bicyclic Products: Stereochemistry

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 Forming Cyclic Products: Stereochemistry

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.

Structure of Conjugated Dienes

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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...

Diels–Alder Reaction: Characteristics of Dienes

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...

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Related Experiment Video

Updated: Sep 5, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Dynamic combinatorial libraries of a dimercapto-pillar[5]arene.

Jinwen Luo¹, Yunlong Guo², Ping Li¹

¹College of Chemistry, Sichuan University, Chengdu, 610064, China. cycheng@scu.edu.cn.

Chemical Communications (Cambridge, England)

|July 13, 2022

Summary

Researchers synthesized a pillar[5]arene with thiol groups, creating a dynamic combinatorial library (DCL). This macrocycle forms cyclic trimers with unique host-guest properties, advancing supramolecular chemistry.

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Last Updated: Sep 5, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Published on: April 19, 2019

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Published on: February 6, 2020

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Area of Science:

Supramolecular Chemistry
Organic Synthesis
Host-Guest Chemistry

Background:

Pillar[5]arenes are macrocyclic hosts with tunable properties.
Dynamic covalent chemistry (DCvC) enables the construction of complex molecular architectures.
Functionalizing macrocycles is key to developing novel materials and systems.

Purpose of the Study:

To synthesize a novel dimercapto-functionalized pillar[5]arene (Di-SH-P5).
To explore the utility of Di-SH-P5 in constructing dynamic combinatorial libraries (DCLs) via DCvC.
To investigate the host-guest properties of the resulting supramolecular assemblies.

Main Methods:

Synthesis of A1/A2-dimercapto-functionalized pillar[5]arene (Di-SH-P5).
Employing dynamic covalent chemistry (DCvC) for library generation.
Characterization of the formed cyclic trimers and their host-guest interactions.

Main Results:

Successful synthesis of Di-SH-P5, a pillar[5]arene bearing two thiol functionalities.
Demonstration of Di-SH-P5 as a versatile building block for DCL formation.
Identification of cyclic trimers as dominant species within the DCL, exhibiting notable host-guest properties.

Conclusions:

The functionalized pillar[5]arene is a valuable component for creating dynamic molecular systems.
DCvC of thiol-functionalized macrocycles provides access to novel supramolecular structures.
The resulting cyclic trimers offer a platform for developing advanced host-guest materials.