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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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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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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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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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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
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

12.8K
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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Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
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Ferrocene- and Biferrocene-Containing Macrocycles towards Single-Molecule Electronics.

Lucy E Wilson1, Christopher Hassenrück2, Rainer F Winter2

  • 1Imperial College of Science, Dept. of Chemistry, South Kensington, London, SW7 2AZ, UK.

Angewandte Chemie (International Ed. in English)
|May 13, 2017
PubMed
Summary

Researchers synthesized novel cyclic compounds containing multiple ferrocene units. These studies explore the electronic interactions and structural effects of cyclization in these multiredox systems.

Keywords:
alkyneselectrochemistryferrocenemacrocyclespectroelectrochemistry

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Area of Science:

  • Organometallic Chemistry
  • Supramolecular Chemistry

Background:

  • Cyclic multiredox systems are gaining significant attention.
  • Understanding their electronic properties and structural behavior is crucial.

Purpose of the Study:

  • To develop efficient synthetic routes for novel alkynyl-conjugated cyclic compounds featuring multiple ferrocene and biferrocene units.
  • To investigate the electronic interactions between ferrocene units within these cyclic structures.

Main Methods:

  • Synthesis of novel cyclic ferrocene and biferrocene compounds.
  • Electrochemical analysis (cyclic voltammetry).
  • Spectroelectrochemical studies.
  • Density Functional Theory (DFT) calculations.
  • X-ray crystallography.

Main Results:

  • Efficient and high-yielding synthetic pathways were established for the target macrocyclic compounds.
  • Electronic interactions between ferrocene units were successfully investigated.
  • The influence of cyclization on electronic properties and molecular structure was elucidated.

Conclusions:

  • The study presents novel cyclic ferrocene-containing compounds with well-defined synthetic routes.
  • Cyclization significantly impacts the electronic properties and structure of multiferrocene systems.
  • This work contributes to the understanding of electron communication in complex organometallic architectures.