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Related Concept Videos

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...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
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...
IUPAC Nomenclature of Ketones01:09

IUPAC Nomenclature of Ketones

Like aldehydes, ketones are named using IUPAC rules; in this case, by replacing “e” in the name of the longest hydrocarbon chain with “one.” In acyclic ketones, the ketonic carbon is given the lowest locant value. For instance, as shown below, a simple five-carbon ketone is named pentan-2-one, instead of pentan-4-one. IUPAC rules also allow the placing of the locant value before the parent name to give an alternate name, 2-pentanone.
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

An in-ketocyclophane.

Qian Qin1, Joel T Mague, Robert A Pascal

  • 1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.

Organic Letters
|February 2, 2010
PubMed
Summary
This summary is machine-generated.

Bulky groups in cyclophanes force carbonyls toward basal rings. Researchers synthesized cyclophane 4, confirming the first in-ketocyclophane structure through X-ray crystallography.

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Crystallography

Background:

  • Benzophenone-capped cyclophanes are studied for their unique structural properties.
  • Conformational restraints can influence the spatial arrangement of functional groups within cyclophanes.
  • Previous computational studies suggested specific orientations for carbonyl groups in such molecules.

Purpose of the Study:

  • To computationally investigate the conformational behavior of benzophenone-capped cyclophanes.
  • To synthesize and structurally characterize a cyclophane exhibiting an 'in-ketocyclophane' conformation.
  • To validate computational predictions with experimental structural data.

Main Methods:

  • Computational modeling to predict molecular conformations.
  • Chemical synthesis of cyclophane 4.
  • X-ray crystallography for detailed structural analysis of cyclophane 4.

Main Results:

  • Computational studies predicted carbonyl groups directed towards basal benzene rings due to steric hindrance.
  • Cyclophane 4 was successfully synthesized.
  • X-ray structure determination confirmed cyclophane 4 as the first 'in-ketocyclophane', with carbonyl groups oriented towards the basal benzene ring.

Conclusions:

  • The study demonstrates the successful synthesis of an in-ketocyclophane.
  • Experimental results validate computational predictions regarding conformational restraints in cyclophanes.
  • This work provides a novel structural motif in cyclophane chemistry.