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Related Concept Videos

Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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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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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.
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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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.
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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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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.
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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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.
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3-Methoxythiophene-Based Indophenine Reaction Generating an Isomeric Dynamic Equilibrium System.

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|April 3, 2023
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Summary

A novel indophenine system was created using a 3-methoxythiophene derivative and N-(2-hexyldecyl)isatin. The reaction predominantly forms the (Z,E,Z) isomer, indicating a specific cis-trans isomeric dynamic equilibrium.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Indophenine synthesis and isomerism are crucial in organic chemistry.
  • Controlling cis-trans isomerism in dynamic systems remains a challenge.

Purpose of the Study:

  • To synthesize and characterize a novel indophenine system.
  • To investigate the cis-trans isomeric dynamic equilibrium of the synthesized indophenine.

Main Methods:

  • A 3-methoxythiophene derivative was reacted with N-(2-hexyldecyl)isatin.
  • Concentrated sulfuric acid was used as a catalyst.
  • Spectroscopic methods were employed to determine isomeric configurations.

Main Results:

  • A dynamic equilibrium system of indophenine cis-trans isomers was successfully produced.
  • The (Z,E,Z) configuration was found to dominate the equilibrium.
  • A minor amount of the (Z,Z,Z) configuration was also detected.

Conclusions:

  • The reaction conditions favor the formation of the (Z,E,Z) indophenine isomer.
  • This study provides insights into controlling isomeric distribution in dynamic systems.
  • The findings contribute to the understanding of indophenine chemistry and isomerism.