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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
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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[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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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.1K
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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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Intramolecular [2 + 2] Photocycloaddition of Benzene Derivatives─Chiral Induction in Cyclodextrin Inclusion

Arthur Desvals1, Corentin Lefebvre2, Agathe Martinez3

  • 1CNRS, Université de Strasbourg, IPCMS, UMR 7504, 23 rue du Loess, 67034 Strasbourg, France.

The Journal of Organic Chemistry
|December 5, 2025
PubMed
Summary

Chiral cyclodextrin complexes enable enantioselective photocycloaddition reactions. Different cyclodextrins induced opposite chirality, significantly increasing enantiomeric excess for valuable chemical synthesis.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Photochemistry

Background:

  • Cyclodextrins (CDs) are cyclic oligosaccharides with a hydrophobic cavity and hydrophilic exterior, widely used in host-guest chemistry.
  • Enantioselective synthesis is crucial for producing single enantiomers of chiral molecules, particularly in pharmaceuticals.
  • Photocycloaddition reactions offer efficient pathways for forming cyclic compounds.

Purpose of the Study:

  • To synthesize and investigate cyclodextrin complexes of butenyloxybenzonitriles.
  • To achieve enantioselective intramolecular [2 + 2] photocycloaddition within these inclusion complexes.
  • To analyze the chiral induction capabilities of different cyclodextrins (α-CD and β-CD).

Main Methods:

  • Synthesis of cyclodextrin complexes with butenyloxybenzonitriles.
  • Irradiation of aqueous suspensions of these inclusion complexes.
  • Analysis of enantiomeric excess (ee) using chiral techniques.
  • Topological analysis and computational studies (energy calculations) of inclusion complexes.

Main Results:

  • Successful synthesis of cyclodextrin complexes and demonstration of enantioselective photocycloaddition.
  • α-Cyclodextrin and β-cyclodextrin induced opposite chiral induction.
  • Significantly increased enantiomeric excess observed at low temperatures (34% for α-CD, -10% for β-CD).
  • Product yield in cyclodextrin complexes (35%) was comparable to racemic reactions in solution (42%).

Conclusions:

  • Cyclodextrin inclusion complexes can effectively mediate enantioselective photocycloaddition reactions.
  • The choice of cyclodextrin host dictates the direction of chiral induction.
  • This method provides a viable route for asymmetric synthesis using readily available cyclodextrins.