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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n + 2 rule.
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.
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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Fusing triazoles: toward extending aromaticity.

Michal Juríček1, Kathleen Stout, Paul H J Kouwer

  • 1Institute for Molecules and Materials, Radboud University Nijmegen, Department of Molecular Materials, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.

Organic Letters
|June 9, 2011
PubMed
Summary
This summary is machine-generated.

Researchers developed a new two-step method to create larger aromatic systems by adding benzene and triazole rings. This technique enhances chromophore size, enabling tunable material properties for advanced applications.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Aromaticity is fundamental to organic chemistry and materials science.
  • Extending aromatic systems is crucial for tuning electronic and optical properties.
  • Current methods for synthesizing extended aromatic cores can be complex and limited.

Purpose of the Study:

  • To develop a novel, efficient synthetic route for extending aromaticity.
  • To create a versatile methodology for synthesizing larger chromophore systems.
  • To enable precise tuning of material properties through controlled extension of aromatic cores.

Main Methods:

  • A two-step synthetic strategy was employed.
  • The first step involved copper-catalyzed azide-haloalkyne cycloaddition of an ortho-bis(iodoacetylene) system.
  • The second step utilized intramolecular homocoupling fusion of neighboring iodotriazoles.

Main Results:

  • Successfully synthesized extended aromatic systems incorporating one benzene and two triazole rings.
  • Demonstrated the formation of an additional benzene ring during the intramolecular homocoupling step.
  • Validated the versatility of the methodology for extending chromophore core sizes.

Conclusions:

  • The developed method provides an efficient route to novel extended aromatic compounds.
  • This approach allows for the systematic enlargement of chromophore frameworks.
  • The tunable nature of the synthesized materials opens avenues for advanced applications in materials science.