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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.9K
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
2.4K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.2K
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.
5.2K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

14.0K
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.
14.0K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.2K
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.
3.2K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

3.7K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
3.7K

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Intramolecular [2 + 2] Photodimerization Achieved in the Solid State via Coordination-Driven Self-Assembly.

Rebecca C Laird1, Michael A Sinnwell1, Nam P Nguyen1

  • 1Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, United States.

Organic Letters
|June 17, 2015
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Summary

Researchers used silver ions and a bipyridine molecule to direct a solid-state organic photocycloaddition reaction. This metal-organic template approach enabled a quantitative and regioselective carbon-carbon double bond reaction.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Photochemistry

Background:

  • Intramolecular [2+2] photocycloadditions are important organic reactions.
  • Controlling these reactions in the solid state remains challenging.
  • Metal-organic frameworks offer potential for directing solid-state reactivity.

Purpose of the Study:

  • To demonstrate the first use of a metal-organic template for intramolecular [2+2] photodimerization in the organic solid state.
  • To investigate the role of Ag(I) ions in organizing reactive components for photocycloaddition.

Main Methods:

  • Self-assembly of silver(I) ions with an endo-ditopic bipyridine ligand.
  • Irradiation of the resulting solid-state material to induce photocycloaddition.
  • Analysis of the photoproduct structure and reaction selectivity.

Main Results:

  • Achieved an intramolecular [2+2] photocycloaddition in the organic solid state.
  • Silver(I) ions effectively organized carbon-carbon double bonds for the reaction.
  • The reaction proceeded with high regioselectivity and quantitative yield.
  • A photoproduct featuring fused four-, five-, and six-membered rings was obtained.

Conclusions:

  • Metal-organic templating is a viable strategy to direct intramolecular [2+2] photocycloadditions in the solid state.
  • This approach offers precise control over reactivity and product formation.
  • The study opens new avenues for designing solid-state photochemical transformations.