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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,...
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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.
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[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.
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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.

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Updated: May 14, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Published on: February 7, 2019

Diastereomeric cyclic tris-allenes.

Hussein H Mustafa1, Mark S Baird, Juma'a R Al Dulayymi

  • 1School of Chemistry, Bangor University, Bangor, Gwynedd, Wales, UK LL57 2UW.

Chemical Communications (Cambridge, England)
|February 20, 2013
PubMed
Summary
This summary is machine-generated.

Researchers synthesized both diastereomers of cyclododeca-1,2,5,6,9,10-hexaene, a tris-allene. This smallest hydrocarbon with D3 symmetry was achieved via a triple cyclopropylidene-allene rearrangement, yielding C2 symmetry in the second diastereomer.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Molecular Symmetry

Background:

  • Cyclic allenes are strained organic molecules.
  • Tris-allenes represent a unique class of cumulenes with potential for novel chemical transformations.
  • Understanding molecular symmetry in hydrocarbons is crucial for predicting chemical and physical properties.

Purpose of the Study:

  • To synthesize both diastereomers of the tris-allene, cyclododeca-1,2,5,6,9,10-hexaene.
  • To characterize the synthesized compounds using spectroscopic methods.
  • To investigate the molecular symmetry of the resulting hydrocarbons.

Main Methods:

  • Triple cyclopropylidene-allene rearrangement reaction.
  • Nuclear Magnetic Resonance (NMR) spectroscopy for structural and symmetry analysis.

Main Results:

  • Successful synthesis of both diastereomers of cyclododeca-1,2,5,6,9,10-hexaene.
  • One diastereomer exhibits D3 symmetry, representing the smallest hydrocarbon synthesized with this symmetry.
  • The second diastereomer was found to possess C2 symmetry.

Conclusions:

  • The triple cyclopropylidene-allene rearrangement is an effective method for synthesizing complex cyclic allenes.
  • The study provides novel examples of hydrocarbons with high symmetry (D3 and C2).
  • These findings contribute to the understanding of stereochemistry and symmetry in polycyclic systems.