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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.
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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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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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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
1.9K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.8K
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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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.5K
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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Updated: Sep 15, 2025

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
09:44

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Published on: October 15, 2019

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A Visible-Light-Responsive Octahedral Cage for Efficient and Selective Cross-[2 + 2] Cycloadditions.

Rikuya Tanaka1, Hiroki Takezawa1, Makoto Fujita2,3

  • 1Department of Applied Chemistry, School of Engineering, The University of Tokyo, Mitsui Link Lab Kashiwanoha 1, FS CREATION, 6-6-2 Kashiwanoha, Kashiwa, Chiba 277-0882, Japan.

Journal of the American Chemical Society
|July 15, 2025
PubMed
Summary

Researchers developed a visible-light-responsive cage for enhanced photoreactions. This cage enables selective cross-[2 + 2] cycloadditions of inert substrates using visible light, even catalytically.

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Area of Science:

  • Supramolecular Chemistry
  • Photochemistry
  • Materials Science

Background:

  • Host-guest complexation influences photoreaction selectivity by confining substrates.
  • Previous hosts lacked visible-light absorption, necessitating UV-absorbing reactants.
  • Standard M6L4 cages are effective hosts but lack photoactivity.

Purpose of the Study:

  • To design a visible-light-responsive M6L4 cage for photoreactions.
  • To enable visible-light-induced cycloadditions of inert substrates.
  • To achieve high stereo- and site-selectivity in photoreactions via confinement.

Main Methods:

  • Development of a visible-light-responsive M6L4 octahedral cage.
  • Incorporation of photoactive cyclometalated Pt(II) units at cage vertices.
  • Utilizing the cage for visible-light-induced cross-[2 + 2] cycloadditions.

Main Results:

  • The new cage retains encapsulation ability while responding to visible light.
  • Efficient visible-light-induced cross-[2 + 2] cycloadditions of inert substrates were achieved.
  • Perfect stereo- and site-selectivity was demonstrated due to substrate confinement.
  • Catalytic selective cross-[2 + 2] cycloaddition was accomplished, a first for M6L4 cages.

Conclusions:

  • Visible-light-responsive M6L4 cages can drive photoreactions with high selectivity.
  • The photoactive Pt(II) units enable unprecedented visible-light-mediated transformations.
  • This approach expands the scope of host-guest chemistry in photochemistry and catalysis.