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Related Concept Videos

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

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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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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...
4.2K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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.
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Preparation of Amides01:29

Preparation of Amides

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

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Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
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PRACTICAL SYNTHESIS OF AROMATIC DITHIOCARBAMATES.

Panuwat Padungros1, Alexander Wei2

  • 1Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand.

Synthetic Communications
|May 23, 2015
PubMed
Summary

Synthesizing oxidation-sensitive N,N-diaryl dithiocarbamates (DTCs) is achieved through metal amide salts and CS2. These DTCs, stable as alkali salts, form dense monolayers on gold surfaces.

Keywords:
Benzamidedeprotectiondithiocarbamateoxidation sensitive

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Surface Chemistry

Background:

  • N,N-diaryl dithiocarbamates (DTCs) are valuable compounds with potential applications in materials science.
  • The synthesis of oxidation-sensitive DTCs presents challenges due to the instability of intermediates.
  • Developing robust synthetic routes is crucial for their practical utilization.

Purpose of the Study:

  • To develop efficient synthetic methods for oxidation-sensitive N,N-diaryl dithiocarbamates (DTCs).
  • To explore the preparation of para-substituted diphenylamines.
  • To investigate the formation of densely packed monolayers on gold surfaces using DTCs.

Main Methods:

  • Synthesis of DTCs via metal amide salts from N-benzoyl precursors and carbon disulfide (CS2).
  • Preparation of para-substituted diphenylamines using electrophilic aromatic substitution and saponification.
  • Employing n-butyllithium (n-BuLi) for deacylation of electron-rich species to form hemiaminal adducts prior to acidification.

Main Results:

  • Good yields of oxidation-sensitive N,N-diaryl dithiocarbamates (DTCs) were achieved.
  • Para-substituted diphenylamines were successfully synthesized.
  • Challenging deacylation of electron-rich species was accomplished using n-BuLi.
  • N,N-diaryl DTCs, stable as alkali salts, were formed.
  • Densely packed monolayers on gold surfaces were produced from the DTC alkali salts.

Conclusions:

  • An effective synthetic strategy for oxidation-sensitive N,N-diaryl dithiocarbamates (DTCs) was established.
  • The synthesized DTCs are stable and suitable for surface modification.
  • The ability to form dense monolayers on gold surfaces opens avenues for applications in nanotechnology and surface science.