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Related Concept Videos

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic factors, steric factors also account...
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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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Related Experiment Video

Updated: May 28, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

pH-Driven dynamic stereoinduction: epimerization upon dimerization in rhenium(I) complexes.

Celedonio M Álvarez1, Romen Carrillo, Raúl García-Rodríguez

  • 1Química Inorgánica, Facultad de Ciencias, Universidad de Valladolid, C/Prado de la Magdalena s/n, E-47071, Valladolid, Spain.

Chemical Communications (Cambridge, England)
|October 11, 2011
PubMed
Summary
This summary is machine-generated.

pH changes alter metal center stereochemistry in Rhenium(I) complexes. Acidic conditions yield monomers, while basic conditions promote dimerization and epimerization.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Last Updated: May 28, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry
  • Coordination Chemistry

Background:

  • Rhenium(I) complexes are valuable in catalysis and materials science.
  • Understanding metal center stereochemistry is crucial for predicting complex behavior.
  • pH-dependent transformations in coordination complexes are not fully elucidated.

Purpose of the Study:

  • To investigate the impact of pH on the stereochemistry of a specific Rhenium(I) complex.
  • To determine the relationship between pH, complex aggregation state, and metal center configuration.
  • To explore the potential for pH-driven stereochemical control in Rhenium(I) systems.

Main Methods:

  • Synthesis and characterization of the Rhenium(I) complex.
  • pH-controlled experiments in solution.
  • Spectroscopic techniques (e.g., NMR, UV-Vis) to monitor changes.
  • Crystallography to determine structural details.

Main Results:

  • Acidic conditions favor a monomeric Rhenium(I) complex.
  • Basic conditions induce dimerization of the Rhenium(I) complex.
  • Dimerization under basic conditions leads to epimerization at the metal center.

Conclusions:

  • The stereochemistry at the Rhenium(I) metal center is sensitive to pH.
  • pH manipulation offers a route to control both aggregation state and stereochemistry.
  • This finding has implications for designing Rhenium(I) complexes with tailored properties.