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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: 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 more stable, the...

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.

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.

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Related Experiment Video

Updated: May 7, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

A durable template for carbosilane dendrimer synthesis.

¹Department of Chemistry, Center for Drug Discovery, Design, and Delivery (CD4), Southern Methodist University, Dallas, TX 75275, USA. dson@smu.edu.

Chemical Communications (Cambridge, England)

|September 24, 2013

Summary

Carbosilane dendrimers are the most studied organosilicon dendrimers. A 1992 communication by Alexander van der Made significantly impacted this field, highlighting their importance in scientific research.

Area of Science:

Organosilicon chemistry
Polymer science
Supramolecular chemistry

Background:

Organosilicon dendrimers represent a diverse class of macromolecules.
Carbosilane dendrimers have garnered significant attention within the scientific community.
Pioneering research has shaped the development of this field.

Purpose of the Study:

To review the impact of a seminal 1992 publication on carbosilane dendrimer research.
To highlight the contributions of Alexander van der Made to the field.
To underscore the significance of carbosilane dendrimers in modern chemistry.

Main Methods:

Literature review focusing on organosilicon dendrimers.
Analysis of the influence of a key 1992 communication.

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Preparation and In Vitro Characterization of Dendrimer-based Contrast Agents for Magnetic Resonance Imaging

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Last Updated: May 7, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Preparation and In Vitro Characterization of Dendrimer-based Contrast Agents for Magnetic Resonance Imaging

Preparation and In Vitro Characterization of Dendrimer-based Contrast Agents for Magnetic Resonance Imaging

Published on: December 4, 2016

Historical perspective on the development of carbosilane dendrimers.

Main Results:

The 1992 publication by Alexander van der Made is recognized as a pivotal moment.
Carbosilane dendrimers have become a primary focus of research within organosilicon chemistry.
The foundational work continues to influence current research directions.

Conclusions:

The impact of early research on carbosilane dendrimers remains substantial.
Carbosilane dendrimers are a key area of ongoing scientific investigation.
Alexander van der Made's contributions are foundational to the field.