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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.0K
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...
3.0K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
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.
2.8K
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.3K
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
2.3K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.3K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.3K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

3.9K
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.
3.9K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.9K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.9K

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Engineering 'Golden' Fluorescence by Selective Pressure Incorporation of Non-canonical Amino Acids and Protein Analysis by Mass Spectrometry and Fluorescence
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α-Diazo-λ

Sven Timmann1, Manuel Alcarazo1

  • 1Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen Tammannstr. 2, 37077 Göttingen, Germany. manuel.alcarazo@chemie.uni-goettingen.de.

Chemical Communications (Cambridge, England)
|June 6, 2023
PubMed
Summary
This summary is machine-generated.

Recent advances in synthetic chemistry include novel reagents for umpolung of diazo compounds. These α-diazo-λ3-iodanes and α-diazo sulfonium salts offer unique reactivity for diverse synthetic applications.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Diazo compounds are versatile synthetic intermediates.
  • Umpolung strategies are crucial for novel bond formations.
  • Development of new reagents expands synthetic possibilities.

Purpose of the Study:

  • To review recent developments in reagents for azomethine carbon umpolung in diazo compounds.
  • To classify the reactivity patterns of these novel reagents.
  • To provide an overview of their synthetic utility.

Main Methods:

  • Literature review of recent advancements.
  • Classification of reagent reactivity.
  • Analysis of synthetic applications.

Main Results:

  • Focus on α-diazo-λ3-iodanes and α-diazo sulfonium salts.
  • Reagents act as carbene-radical or carbene-carbocation synthons.
  • Detailed discussion of preparation routes and reactivity.

Conclusions:

  • These reagents represent significant progress in diazo chemistry.
  • Their unique reactivity offers new synthetic pathways.
  • Critical comparison highlights their potential and limitations.