Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
[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.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Cycloalkanes02:28

Cycloalkanes

Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the...
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,...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

A Review on the Synthetic Methods towards Benzothienobenzothiophenes.

Chemical record (New York, N.Y.)·2024
Same author

[2.2]Paracyclophane Derivatives as Building Blocks for Coordination Polymers.

Materials (Basel, Switzerland)·2023
Same author

Chemistry must respond to the crisis of transgression of planetary boundaries.

Chemical science·2022
Same author

A shared future: chemistry's engagement is essential for resilience of people and planet.

Royal Society open science·2022
Same author

Re-imagining Priorities for Chemistry: A Central Science for "Freedom from Fear and Want".

Angewandte Chemie (International ed. in English)·2021
Same author

Crystal structure of <i>N</i>'-[2-(benzo[<i>d</i>]thia-zol-2-yl)acet-yl]benzohydrazide, an achiral compound crystallizing in space group <i>P</i>1 with <i>Z</i> = 1.

Acta crystallographica. Section E, Crystallographic communications·2021

Related Experiment Video

Updated: Jul 9, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

The 'cyclophene' [2.2.2](1,2,4)cyclophan-9-ene.

Klaus Broschinski1, Arunachalam Kannan, Peter G Jones

  • 1Institut für Organische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany.

Acta Crystallographica. Section C, Crystal Structure Communications
|December 7, 2007
PubMed
Summary

This study details a novel [2.2]paracyclophane derivative with an added C=C bridge. Despite structural modifications, it retains typical paracyclophane features while exhibiting unique geometric constraints and molecular packing.

More Related Videos

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

Related Experiment Videos

Last Updated: Jul 9, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • Paracyclophanes are cyclic hydrocarbons with benzene rings linked by bridges.
  • Structural modifications of paracyclophanes can alter their geometric and electronic properties.
  • Understanding these modifications is key to designing novel molecular architectures.

Purpose of the Study:

  • To synthesize and characterize a novel [2.2]paracyclophane derivative featuring an additional C=C bridge.
  • To investigate the impact of the C=C bridge on the geometry and crystal packing of the paracyclophane system.
  • To analyze the structural consequences of restrained geometry in [2.2]paracyclophanes.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular structure.
  • Crystallographic data were analyzed to ascertain bond lengths, angles, and interplanar distances.
  • Molecular packing in the solid state was examined.

Main Results:

  • The synthesized compound, C18H16, exhibits a [2.2]paracyclophane core with an additional C=C bridge.
  • The geometry is significantly restrained, with bridgehead atoms of the C=C bridge in close proximity (2.657 Å).
  • An interplanar angle of 13.7 degrees between the aromatic rings was observed, alongside typical elongated C-C bridges.
  • Hexagonally close-packed layers with a '7,11' pattern were noted, lacking significant short intermolecular contacts.

Conclusions:

  • The introduction of a C=C bridge in [2.2]paracyclophanes leads to notable geometric distortions and restrained conformations.
  • The study provides insights into the structure-property relationships of modified paracyclophane systems.
  • The observed molecular packing highlights specific intermolecular interactions in this class of compounds.