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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

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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...
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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
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...
3.5K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.2K
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.
3.2K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

3.0K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
3.0K
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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Azaacenodibenzosuberones.

Victor Brosius1, Matthias Müller1, Jan Borstelmann1

  • 1Organisch-Chemisches Institut , Ruprecht-Karls-Universität Heidelberg , Im Neuenheimer Feld 270 , 69120 Heidelberg , Germany.

The Journal of Organic Chemistry
|November 6, 2019
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel N-heteroacenes by reacting dibenzosuberonetriketone with diaminoarenes. These electron-deficient compounds, featuring pyrazine or bis-pyrazine cores, were formed efficiently at room temperature and exhibited negative curvature.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Dibenzosuberone derivatives are versatile building blocks in organic synthesis.
  • N-heteroacenes are important scaffolds for electronic and optical materials.
  • Controlling molecular curvature is key to designing advanced functional materials.

Purpose of the Study:

  • To synthesize novel dibenzosuberone-fused N-heteroacenes.
  • To investigate the condensation reaction between dibenzosuberonetriketone and substituted aminoarenes.
  • To characterize the structural and electronic properties of the resulting N-heteroacenes.

Main Methods:

  • Condensation reaction of dibenzosuberonetriketone with various diamino- and tetramino-arenes.
  • Room temperature reaction conditions.
  • Single crystal X-ray diffraction for structural analysis.

Main Results:

  • A series of dibenzosuberone-fused N-heteroacenes were successfully synthesized.
  • The condensation reaction proceeded with good to excellent yields.
  • The synthesized compounds, containing pyrazine or bis-pyrazine units, exhibited negative curvature in their solid-state structures.

Conclusions:

  • Dibenzosuberonetriketone is an effective precursor for constructing complex N-heteroacene architectures.
  • The reaction offers a facile route to electron-deficient N-heteroacenes with tunable properties.
  • The observed negative curvature suggests potential applications in areas requiring specific molecular geometries, such as organic electronics.