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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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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...
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.6K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.4K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.4K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.3K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.3K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Updated: Jan 14, 2026

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Donor-Acceptor-Substituted 5-Azaazulenes.

Enikő Meiszter1,2, Gábor Turczel3, András Stirling1,4

  • 1Institute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, 1117 Budapest, Hungary.

The Journal of Organic Chemistry
|October 17, 2025
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel 5-azaazulenes via ring expansion of azapentalenes. These compounds, featuring donor and acceptor groups, show potential for organic photonics applications.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Computational Chemistry

Background:

  • Azulenes and their aza-analogs are known for unique electronic properties.
  • Developing novel heterocyclic compounds is crucial for advanced materials.
  • Organic photonics requires tailored molecular structures with specific photophysical properties.

Purpose of the Study:

  • To report the synthesis of 5-azaazulenes with donor and acceptor substituents.
  • To investigate the reaction mechanism and regioselectivity of the ring expansion.
  • To explore the potential of these compounds in organic photonics.

Main Methods:

  • Ring expansion of stable azapentalene derivatives.
  • Reaction with dimethyl acetylenedicarboxylate.
  • Characterization of regioisomeric products.
  • Computational studies on reaction mechanisms and excited state energy levels.

Main Results:

  • Successful synthesis of 5-azaazulenes with diverse substituents.
  • Obtained and characterized regioisomeric products.
  • Elucidated the transformation mechanism through computational analysis.
  • Determined excited state energy levels of the synthesized compounds.

Conclusions:

  • The developed method provides access to functionalized 5-azaazulenes.
  • The synthesized compounds exhibit properties suitable for chromophore design.
  • These 5-azaazulenes represent promising building blocks for organic photonics.