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Related Concept Videos

Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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,...
Thermal Electrocyclic Reactions: Stereochemistry01:17

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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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Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.

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Updated: May 18, 2026

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Solvent-catalyzed ring-chain-ring tautomerization in axially chiral compounds.

Asli Yildirim1, Fethiye Aylin Sungur Konuklar, Saron Catak

  • 1Department of Chemistry, Boğaziçi University, Bebek, Istanbul, Turkey.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 15, 2012
PubMed
Summary

Computational studies reveal the mechanism of ring-chain-ring tautomerization in 2-oxazolidinones. Polar protic solvents significantly influence this process, crucial for developing stable axially chiral catalysts.

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Catalysis

Background:

  • 2-oxazolidinone derivatives, analogous to biphenyl atropisomers, exhibit enantiomeric interconversion.
  • These compounds are isolated as single enantiomers and show potential as axially chiral catalysts.
  • Understanding their tautomerization is key to maintaining enantiomeric stability.

Purpose of the Study:

  • To computationally investigate the ring-chain-ring tautomerization mechanism in 2-oxazolidinone derivatives.
  • To elucidate the significant effect of the solvent environment on this tautomerization process.
  • To explain the observed enantiomeric interconversion and guide catalyst development.

Main Methods:

  • Computational investigation of reaction mechanisms.
  • Analysis of solvent effects, particularly polar protic solvents.
  • Identification of intermediate species in the tautomerization pathway.

Main Results:

  • The study identified key intermediate species involved in the ring-chain-ring tautomerization.
  • Demonstrated the pronounced catalytic effect of polar protic solvents on the tautomerization.
  • Provided mechanistic insights into the enantiomeric interconversion of 2-oxazolidinone derivatives.

Conclusions:

  • Mechanistic details of ring-chain tautomerization are elucidated.
  • Polar protic solvents play a critical role in mediating tautomeric equilibria.
  • Findings aid in predicting tautomeric behavior and designing stable axially chiral catalysts.