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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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Stereoisomerism

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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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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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UV–Vis Spectroscopy: Woodward–Fieser Rules01:29

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UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the...
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Stereoisomerism of Cyclic Compounds02:33

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Modifying Woodward-Hoffmann Stereoselectivity Under Vibrational Strong Coupling.

Abhijit Sau1, Kalaivanan Nagarajan1, Bianca Patrahau1

  • 1University of Strasbourg, CNRS, ISIS & icFRC, 67000, Strasbourg, France.

Angewandte Chemie (International Ed. in English)
|December 11, 2020
PubMed
Summary
This summary is machine-generated.

Vibrational strong coupling (VSC) can control chemical reactions by altering stereoselectivity in pericyclic reactions. The specific vibrational mode coupled dictates changes in reaction outcomes, highlighting symmetry

Keywords:
Woodward-Hoffmann ruleselectrocyclic ring openingorbital symmetrypericyclic reactionsstrong coupling

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Area of Science:

  • Chemical Physics
  • Physical Chemistry
  • Quantum Chemistry

Background:

  • Vibrational strong coupling (VSC) modifies chemical reactions by forming light-matter hybrid polaritonic states.
  • Symmetry of vibrational modes influences charge-transfer reactions under VSC, suggesting broader control over chemical selectivity.

Purpose of the Study:

  • To investigate the influence of VSC on the stereoselectivity of pericyclic reactions, specifically the thermal electrocyclic ring opening of cyclobutene derivatives.
  • To determine if vibrational mode symmetry can be leveraged to control stereoselectivity in these reactions.

Main Methods:

  • Experimental investigation of the thermal electrocyclic ring opening of a cyclobutene derivative under conditions of VSC.
  • Analysis of changes in stereoselectivity, reaction rate, and thermodynamics based on the coupled vibrational mode.

Main Results:

  • VSC was shown to influence the stereoselectivity of the cyclobutene ring-opening reaction.
  • The direction of stereoselectivity change was dependent on the specific vibrational mode coupled during VSC.
  • Changes in reaction rate and thermodynamics were also observed and correlated with the coupled vibrational mode.

Conclusions:

  • Symmetry considerations play a crucial role in controlling chemical reactivity under VSC, extending beyond charge-transfer reactions.
  • VSC offers a potential pathway to control the stereochemical outcomes of pericyclic reactions by tuning vibrational modes.