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

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

12.1K
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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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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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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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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Synthesis and Characterization of Functionalized Metal-organic Frameworks
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Linkage Multi-functionalization in Covalent Organic Frameworks via Criss-Cross 1,3-Dipolar Cycloaddition.

Hui-Hui Sun1, Xi-Jun Wen1, Zhi-Bei Zhou1

  • 1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, China.

Angewandte Chemie (International Ed. in English)
|October 24, 2025
PubMed
Summary

Researchers developed a new method to add multiple functional groups to covalent organic frameworks (COFs) in one step. This linkage conversion strategy enhances COF properties for diverse applications.

Keywords:
1,3‐Dipolar cycloadditionAzine linkageCovalent organic frameworksLinkage transformationMulti‐functionalization

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Microfluidic-based Synthesis of Covalent Organic Frameworks COFs: A Tool for Continuous Production of COF Fibers and Direct Printing on a Surface
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Microfluidic-based Synthesis of Covalent Organic Frameworks COFs: A Tool for Continuous Production of COF Fibers and Direct Printing on a Surface

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Area of Science:

  • Materials Science
  • Polymer Chemistry
  • Organic Chemistry

Background:

  • Functionalization of covalent organic frameworks (COFs) is crucial for tailoring their properties and applications.
  • Multi-functionalization strategies for polymers, especially COFs, are underdeveloped, limiting their potential.
  • Azine-linked COFs offer a platform for post-synthetic modification.

Purpose of the Study:

  • To develop a novel and general strategy for simultaneous multi-functionalization of azine-linked COFs.
  • To demonstrate the versatility of the strategy in introducing diverse functional groups into COFs.
  • To enable the creation of highly functionalized COFs for advanced applications.

Main Methods:

  • Utilizing a criss-cross 1,3-dipolar cycloaddition reaction between azine linkages in COFs and multifarious alkynes.
  • Employing alkynes with different functional groups to achieve simultaneous homo-type and hetero-type functionalization.
  • Synthesizing and characterizing over 10 different functionalized COFs.

Main Results:

  • Successfully demonstrated a novel linkage conversion strategy for COF functionalization.
  • Achieved simultaneous introduction of multiple, diverse functional groups into azine-linked COFs.
  • Constructed more than 10 distinct functionalized COFs, showcasing the method's broad applicability and high efficiency.

Conclusions:

  • The developed strategy provides a powerful and general tool for dense functional group introduction into COFs.
  • This method significantly expands the possibilities for designing COFs with specific properties.
  • The functionalized COFs are poised for further exploration in various application domains.