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

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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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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.

Chemical Reactions

Chemical Reactions

A chemical reaction is a process by which the bonds in the atoms of substances are rearranged to generate new substances. Matter cannot be created or destroyed in a chemical reaction—the same type and number of atoms that make up the reactants are still present in the products. Merely, the rearrangement of chemical bonds produces new compounds.
Chemical Reactions Rearrange Atoms into New Substances
A chemical reaction takes starting materials—the reactants—and changes them...

Chemical Reactions

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A balanced chemical equation provides the information of chemical formulas of the reactants and products involved in the chemical change. A reaction’s stoichiometry helps predict how much of the reactant is needed to produce the desired amount of product, or in some cases, how much product will be formed from a specific amount of the reactant.
The relative amounts of reactants and products represented in a balanced chemical equation are often referred to as stoichiometric amounts. However, in...

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Related Experiment Video

Updated: Dec 9, 2025

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Published on: January 4, 2018

Chemodivergent reactions.

Irina P Beletskaya¹, Carmen Nájera, Miguel Yus

¹Chemistry Department, M. V. Lomonosov Moscow University, Leminskie Gory 1, 119992 Moscow, Russia.

Chemical Society Reviews

|September 14, 2020

Summary

Chemodivergent transformations enable diverse molecular structures from common starting materials. Controlling reaction conditions like catalysts and solvents dictates product outcomes in various synthetic processes.

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Efficient generation of molecular diversity is crucial in chemistry.
Chemodivergent transformations utilize common starting materials to access varied molecular structures.
Controlling chemoselectivity is key, influenced by catalysts, ligands, solvents, and temperature.

Purpose of the Study:

To review various chemodivergent transformations.
To highlight how reaction parameters influence selectivity.
To showcase the synthesis of diverse cyclic and acyclic compounds.

Main Methods:

Review of literature on inter- and intramolecular cyclizations (carba-, oxa-, thia-, oxazacyclizations).
Analysis of cycloaddition reactions ((2+2) to (7+2) processes).
Examination of addition, carbonylation, ring-opening, reduction, oxidation, and cross-coupling reactions.

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Chemical Gardens as Flow-through Reactors Simulating Natural Hydrothermal Systems

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

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Last Updated: Dec 9, 2025

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Published on: January 4, 2018

Chemical Gardens as Flow-through Reactors Simulating Natural Hydrothermal Systems

Chemical Gardens as Flow-through Reactors Simulating Natural Hydrothermal Systems

Published on: November 18, 2015

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

Main Results:

Catalyst-controlled cyclizations yield five- and six-membered rings.
Cycloadditions, additions, carbonylations, and ring-opening reactions produce diverse cyclic and acyclic products.
Reductions, oxidations, and cross-coupling reactions offer further synthetic versatility.

Conclusions:

Reaction parameters like catalysts and solvents are critical for controlling chemoselectivity in transformations.
Chemodivergent strategies provide efficient access to a wide array of molecular architectures.
This review consolidates key methods for generating molecular diversity through controlled chemical reactions.