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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.5K
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.
3.5K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
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.
2.5K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.1K
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.
10.1K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.8K
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.
3.8K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.0K
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.
2.0K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.1K
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).
2.1K

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Updated: Jun 16, 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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A solid noncovalent organic double-helix framework catalyzes asymmetric [6 + 4] cycloaddition.

Tianyu Zheng1, Nils Nöthling1, Zikuan Wang1

  • 1Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany.

Science (New York, N.Y.)
|August 15, 2024
PubMed
Summary

Chemists developed a novel double helix-shaped catalyst from a noncovalent organic framework. This catalyst enables challenging [6 + 4] cycloadditions, offering a new route to valuable 10-membered rings.

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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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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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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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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Supramolecular Chemistry

Background:

  • [4 + 2] cycloadditions are versatile synthetic tools.
  • Controlling reactivity and selectivity in [6 + 4] cycloadditions remains a significant challenge.
  • Accessing 10-membered rings via cycloaddition is synthetically valuable but difficult.

Purpose of the Study:

  • To develop a general and selective method for [6 + 4] cycloadditions.
  • To explore the catalytic potential of novel imidodiphosphorimidate-derived frameworks.
  • To enable the synthesis of complex 10-membered ring structures from simple substrates.

Main Methods:

  • Design and synthesis of highly acidic imidodiphosphorimidate catalysts.
  • Observation of spontaneous precipitation into a double helix-shaped noncovalent organic framework (COF).
  • Utilizing the insoluble COF as a heterogeneous catalyst for [6 + 4] cycloadditions.

Main Results:

  • The insoluble COF catalyst demonstrated high reactivity and stereoselectivity in [6 + 4] cycloadditions.
  • The reaction involved simple dienes and tropone, yielding 10-membered rings.
  • Homogeneous catalysis with the precursor imidodiphosphorimidate was unsuccessful.

Conclusions:

  • Imidodiphosphorimidate-derived COFs can act as effective heterogeneous catalysts for challenging [6 + 4] cycloadditions.
  • This work presents a novel catalytic system for constructing 10-membered rings with high selectivity.
  • The self-assembly of a reactive framework from a molecular precursor offers a new strategy in catalysis.