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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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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.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[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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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Updated: Dec 15, 2025

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Flow Chemistry for Cycloaddition Reactions.

Jorge García-Lacuna1, Gema Domínguez1, Javier Pérez-Castells1

  • 1Department of Chemistry and Biochemistry, Facultad de Farmacia, Universidad San Pablo-CEU, CEU Universities Urbanización Montepríncipe, 28660, Boadilla del Monte, Madrid, Spain.

Chemsuschem
|July 15, 2020
PubMed
Summary
This summary is machine-generated.

Continuous flow reactors offer safer, scalable, and efficient methods for cycloaddition reactions. These advanced techniques are revolutionizing synthetic chemistry in both academic and industrial settings.

Keywords:
carbocyclescycloadditionflow chemistryheterocyclesmicroreactors

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Area of Science:

  • Synthetic Chemistry
  • Chemical Engineering

Background:

  • Continuous flow reactors are transforming synthetic chemistry.
  • Cycloaddition reactions are vital for synthesizing complex molecules.
  • Flow chemistry offers advantages like intensified conditions and safer handling of hazardous materials.

Purpose of the Study:

  • To review recent advances in cycloaddition reactions within flow systems.
  • To highlight the benefits of using flow chemistry for various cycloaddition types.
  • To emphasize the industrial relevance of these flow-based transformations.

Main Methods:

  • Review of recent literature on flow chemistry and cycloaddition reactions.
  • Analysis of key cycloaddition reactions amenable to flow systems.
  • Discussion of advantages including safety, efficiency, and scalability.

Main Results:

  • Flow systems enable intensified conditions and safer handling of hazardous reagents for cycloadditions.
  • Key cycloadditions like copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), Diels-Alder, ozonolysis, and [2+2] photocycloadditions benefit significantly from flow implementation.
  • Flow chemistry facilitates straightforward tuning of reaction conditions and scaling up.

Conclusions:

  • Flow chemistry provides significant advantages for performing cycloaddition reactions.
  • These advancements are crucial for the efficient and safe synthesis of complex molecular structures.
  • The application of flow cycloadditions is particularly impactful in pharmaceutical manufacturing.