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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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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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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.
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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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Chair Conformation of Cyclohexane02:02

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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photodriven [2]rotaxane-[2]catenane interconversion.

Arnaud Tron1, Henri-Pierre Jacquot de Rouville, Aurélien Ducrot

  • 1Institut des Sciences Moléculaires, CNRS UMR 5255, Univ. Bordeaux, 33405 Talence, France. nathan.mcclenaghan@u-bordeaux.fr.

Chemical Communications (Cambridge, England)
|January 14, 2015
PubMed
Summary
This summary is machine-generated.

This study demonstrates a novel photocatenation process for mechanically interlocked molecules. A rotaxane transforms into a catenane using reversible anthracene photocycloaddition.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Photochemistry

Background:

  • Mechanically Interlocked Molecules (MIMs) are complex architectures with unique properties.
  • Rotaxanes and catenanes are key classes of MIMs, with applications in molecular machines and materials.
  • Controlling topology interconversion in MIMs is crucial for advanced functional systems.

Purpose of the Study:

  • To achieve efficient topology interconversion between [2]rotaxane and [2]catenane structures.
  • To utilize photocycloaddition reactions for controlled molecular transformations.
  • To explore the reversible nature of anthracene-based photocycloaddition in MIMs.

Main Methods:

  • Synthesis of a specific [2]rotaxane featuring dibenzylammonium and 9-alkoxyanthracene units.
  • Complexation of the rotaxane's thread with a 24-dibenzo-8-crown-6 ether ring.
  • Irradiation to induce [4π+4π] photocycloaddition of the terminal anthracene groups, leading to photocatenation.

Main Results:

  • An efficient photocatenation reaction was achieved, converting the [2]rotaxane to a [2]catenane.
  • The topology interconversion was driven by a reversible [4π+4π] photocycloaddition of anthracene moieties.
  • The process demonstrated high efficiency in the transformation of molecular architecture.

Conclusions:

  • Photocatenation offers a viable strategy for the synthesis of complex MIMs.
  • Reversible anthracene photocycloaddition is a powerful tool for manipulating molecular topology.
  • This work advances the design and synthesis of switchable supramolecular systems.