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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.8K
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

3.7K
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.
3.7K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.4K
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.
10.4K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
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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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.5K
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...
8.5K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.3K
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).
2.3K

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Updated: Sep 6, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Cycloparaphenylenes via [2+2+2] cycloaddition.

Daniel Kohrs1,2, Jannis Volkmann1,2, Hermann A Wegner1,2

  • 1Institute of Organic Chemistry, Justus Liebig University Giessen, Heinrich-Buff-Ring 17, 35392 Giessen, Germany. Hermann.A.Wegner@org.Chemie.uni-giessen.de.

Chemical Communications (Cambridge, England)
|June 24, 2022
PubMed
Summary
This summary is machine-generated.

The [2+2+2] cycloaddition is a versatile method for creating substituted aromatic rings. This review explores its use in synthesizing cycloparaphenylenes, detailing strategies and their advantages.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • The [2+2+2] cycloaddition (CA) is an atom-economic reaction for forming substituted aromatic rings.
  • Cycloparaphenylenes (CPPs) are important molecular architectures with unique properties.

Purpose of the Study:

  • To highlight the application of the [2+2+2] CA in synthetic strategies for substituted CPPs.
  • To categorize and analyze different synthetic approaches based on the role of the [2+2+2] CA.

Main Methods:

  • Review of synthetic methodologies employing [2+2+2] cycloaddition for CPP synthesis.
  • Categorization of strategies into four classes based on the CA's function (aromatization, macrocyclization, or both).

Main Results:

  • The [2+2+2] CA can be strategically employed at different stages of CPP synthesis.
  • Analysis of the benefits and drawbacks associated with each synthetic strategy.

Conclusions:

  • The [2+2+2] CA is a powerful tool for constructing substituted CPPs.
  • Understanding the different strategic roles of the CA facilitates efficient synthesis design.