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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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¹H NMR: Long-Range Coupling01:27

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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
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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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Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

1.0K
Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
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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.
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Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
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Electronic Coupling in Triferrocenylpnictogens.

Corina Stoian1, Fawaz Al Hussein1, Wesley R Browne2

  • 1Institute for Inorganic Chemistry and Crystallography, Faculty of Biology and Chemistry, University of Bremen, Leobener Straße 7, Bremen 28359, Germany.

ACS Organic & Inorganic Au
|October 7, 2024
PubMed
Summary
This summary is machine-generated.

Researchers studied novel mixed-valent ferrocenyl complexes, specifically triferrocenylpnictogens (Fc3E). They found weak electronic couplings in related cations, suggesting a through-space electron transfer mechanism.

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Area of Science:

  • Organometallic Chemistry
  • Electrochemistry
  • Materials Science

Background:

  • Mixed-valent complexes with ferrocenyl units are crucial for advancing electron transfer theories.
  • The series of triferrocenylpnictogens (Fc3E) was extended to heavier analogues (E = As, Sb, Bi).

Purpose of the Study:

  • To investigate the influence of the bridging atom (As, Sb, Bi) on the electronic properties of triferrocenylpnictogens.
  • To understand the factors contributing to large redox splitting in these compounds.

Main Methods:

  • Electrochemical studies to analyze redox splitting (ΔE1).
  • Structural characterization of the synthesized compounds.
  • Spectroelectrochemical studies to probe electronic coupling.

Main Results:

  • Electrochemical studies revealed the significant impact of electrostatic contributions on redox splitting.
  • Solvent stabilization effects were observed for Fc3As.
  • Structural and spectroelectrochemical data indicated weak electronic couplings in the [Fc3E]+ cations.

Conclusions:

  • The bridging atom significantly influences the electrochemical properties of triferrocenylpnictogens.
  • A through-space mechanism is proposed for electron transfer in the oxidized species due to weak electronic coupling.