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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.

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...

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.

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.

Radical Chain-Growth Polymerization: Chain Branching

Radical Chain-Growth Polymerization: Chain Branching

The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...

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Updated: Jun 22, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Published on: September 18, 2016

Calix[4]arene daisychains.

Soheila Sameni¹, Catherine Jeunesse, Dominique Matt

¹Université de Strasbourg, Laboratoire de Chimie Inorganique Moléculaire et Catalyse, UMR 7177 CNRS, Strasbourg cedex, France.

Chemical Society Reviews

|June 25, 2009

Summary

This summary is machine-generated.

Multicalixarene compounds, featuring linked calixarene units, offer unique properties for molecular recognition and sensing. The linkage strategy is crucial for their application in host-guest chemistry and material science.

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Area of Science:

Supramolecular Chemistry
Organic Synthesis

Background:

Calix[4]arenes, macrocyclic compounds with multiple anchoring points, have been synthesized since the 1970s.
Research is increasingly focusing on multicalixarene compounds, particularly those with linearly arranged calix[4]arene units, first reported in 1989.

Purpose of the Study:

To review synthetic routes for multicalixarene compounds.
To analyze how combined cavities influence molecular properties.
To highlight the role of linking groups in determining product characteristics.

Main Methods:

Review of synthetic methodologies for multicalixarene construction.
Analysis of structure-property relationships in linked calixarene systems.

Main Results:

Singly-linked calixarenes demonstrate significant potential.
These compounds function as effective receptors for large molecules.
Applications include ion detection via electrochemical and luminescent sensing, and capsule formation for guest storage.

Conclusions:

The nature of the linkage between calixarene units is critical for their properties.
Multicalixarenes offer diverse applications in molecular recognition, sensing, and materials science.