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Related Concept Videos

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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Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

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Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
2.2K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.1K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.1K
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
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.
3.7K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
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.
2.2K

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Controllable multiple-step configuration transformations in a thermal/photoinduced reaction.

Meng-Fan Wang1, Yan Mi2, Fei-Long Hu3

  • 1College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu, People's Republic of China.

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|May 23, 2022
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This study introduces a novel method for controlling stereochemistry in solid-state photochemical reactions using temperature variations. This enables reversible ring transformations in coordination polymers, offering precise control over organic cyclic molecule synthesis.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Solid-state photochemical reactions offer a route to complex organic cyclic molecules.
  • Precise stereochemical control in these reactions is challenging due to complex transformations.

Purpose of the Study:

  • To develop a method for controlling regiospecific configurations in olefinic compounds.
  • To achieve reversible ring closing/opening reactions using a single-crystal coordination polymer platform.

Main Methods:

  • Utilizing multiple-step thermal/photoinduced reactions with temperature variations.
  • Employing in situ single-crystal X-ray diffraction, powder X-ray diffraction, and infrared spectroscopy.
  • Performing density functional theory calculations to elucidate reaction mechanisms.

Main Results:

  • Demonstrated precise control over the stereochemistry of C=C groups and intermediates.
  • Successfully achieved reversible ring closing and opening transformations.
  • Rationalized the mechanism of synergistic thermal/photoinduced transformations.

Conclusions:

  • The developed approach allows for controlled stereochemical transitions in solid-state reactions.
  • This method provides a versatile platform for analyzing reaction mechanisms in various materials.
  • The findings advance the understanding and application of photochemical reactions in materials science.