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Related Concept Videos

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
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,...
2.1K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

1.8K
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...
1.8K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

2.9K
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...
2.9K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.7K
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.
2.7K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

4.7K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
4.7K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

3.7K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
3.7K

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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An Isolable Base-Stabilized Diazosilenyl Cation.

Shintaro Takahashi1, Aurora Rodríguez-Álvarez1, Antoine Baceiredo1

  • 1Université de Toulouse, UPS, and CNRS, LHFA UMR 5069 188 route de Narbonne, 31062, Toulouse, France.

Angewandte Chemie (International Ed. in English)
|December 6, 2024
PubMed
Summary

Researchers synthesized a stable diazosilenyl cation, a silicon analog of diazoalkenes. This novel compound exhibits unique stability and dual reactivity, paving the way for new organosilicon chemistry.

Keywords:
diazo compoundsdiazoalkenesdiazosilenessilylenessilynes

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Area of Science:

  • Organosilicon Chemistry
  • Main Group Chemistry
  • Reactive Intermediates

Background:

  • Stable diazoalkenes are an emerging class of compounds.
  • Heavier silicon analogues, known as diazosilenes, have not been previously studied.

Purpose of the Study:

  • To synthesize and characterize the first stable diazosilenes.
  • To investigate the stability and reactivity of these novel silicon compounds.

Main Methods:

  • Synthesis of a base-stabilized diazosilenyl cation via reaction of a C-phosphonio-silyne with N2O.
  • Density Functional Theory (DFT) calculations to predict electronic properties and reactivity.

Main Results:

  • A stable, base-stabilized diazosilenyl cation was successfully synthesized.
  • The silicon analog of diazoalkenes exhibits remarkable stability due to phosphine and phosphine oxide ligand coordination.
  • DFT calculations suggest that π-donor substituents are not essential for preventing N2 dissociation in diazosilenes, unlike carbon analogues.
  • The diazosilenyl cation isomerizes to a (silylene)(phosphonio)diazomethane, showing dual reactivity.

Conclusions:

  • The first stable diazosilenes have been synthesized and characterized.
  • These compounds possess unique stability and reactivity profiles, distinct from their carbon counterparts.
  • The findings open new avenues in organosilicon chemistry and the study of reactive intermediates.