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Related Concept Videos

Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
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Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
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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...
Oxidation Numbers03:14

Oxidation Numbers

In redox reactions, the transfer of electrons occurs between reacting species. Electron transfer is described by a hypothetical number called the oxidation number (or oxidation state). It represents the effective charge of an atom or element, which is assigned using a set of rules.

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Odd-numbered oxacalix[n]arenes (n = 5, 7): synthesis and solid-state structures.

Wim Van Rossom1, Koen Robeyns, Magriet Ovaere

  • 1Molecular Design and Synthesis, Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.

Organic Letters
|December 7, 2010
PubMed
Summary

Researchers developed a new method to synthesize odd-numbered oxacalixarenes (n=5, 7) using nucleophilic aromatic substitution. This work provides access to these less-studied macrocycles for potential applications in molecular recognition.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Macrocyclic Chemistry

Background:

  • Odd-numbered calix[n]arenes are less studied macrocycles despite exhibiting unique molecular recognition properties.
  • Existing synthetic routes for these compounds are often challenging, limiting their accessibility.

Purpose of the Study:

  • To develop a straightforward and selective synthetic strategy for odd-numbered oxacalix[n]arenes.
  • To investigate the structural and conformational characteristics of the synthesized odd-numbered oxacalix[n]arenes.

Main Methods:

  • A fragment coupling approach utilizing kinetically controlled nucleophilic aromatic substitution.
  • Synthesis of odd-numbered oxacalix[n]arenes with n=5 and n=7.
  • Single-crystal X-ray diffraction studies to analyze solid-state conformation and cavity size.

Main Results:

  • Selective synthesis of odd-numbered oxacalix[n]arenes (n=5, 7) in high yields.
  • Demonstration of a straightforward fragment coupling strategy for accessing these macrocycles.
  • Characterization of the solid-state structures and cavity dimensions of the synthesized compounds.

Conclusions:

  • The developed method provides efficient access to valuable odd-numbered oxacalixarene building blocks.
  • This synthetic advancement facilitates further exploration of their molecular recognition capabilities.
  • Structural insights were gained into the conformational preferences and cavity properties of these macrocycles.