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Related Concept Videos

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
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
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.3K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.3K
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
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.1K
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.
2.1K
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

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Nitrous oxide as diazo transfer reagent.

Alexandre Genoux1, Kay Severin1

  • 1Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL) 1015 Lausanne Switzerland kay.severin@epfl.ch.

Chemical Science
|August 19, 2024
PubMed
Summary
This summary is machine-generated.

Nitrous oxide (N₂O) is a versatile chemical reagent. Beyond oxidation, it efficiently transfers diazo groups, enabling synthesis of triazenes, N-heterocycles, and azo compounds.

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Area of Science:

  • Chemistry
  • Organic Synthesis
  • Green Chemistry

Background:

  • Nitrous oxide (N₂O), or "laughing gas", is a common industrial byproduct and can be produced from ammonium nitrate decomposition.
  • Traditionally, N₂O is utilized in oxidation reactions as an oxygen atom transfer reagent.
  • Emerging research explores alternative chemical transformations of N₂O.

Purpose of the Study:

  • To review recent advancements in the chemical valorization of nitrous oxide (N₂O).
  • To highlight N₂O's emerging role as a diazo transfer reagent.
  • To summarize novel synthetic methodologies developed using N₂O.

Main Methods:

  • Literature review of recent scientific publications.
  • Analysis of synthetic pathways utilizing N₂O as a diazo transfer reagent.
  • Compilation of methods for synthesizing triazenes, N-heterocycles, and azo-compounds.

Main Results:

  • N₂O demonstrates significant potential as an efficient diazo transfer reagent.
  • Development of synthetically valuable methods for producing triazenes.
  • Successful synthesis of N-heterocycles and azo-compounds using N₂O-mediated reactions.

Conclusions:

  • Nitrous oxide offers a novel and efficient pathway for diazo transfer reactions.
  • This emerging field provides new synthetic tools for organic chemistry.
  • Further exploration of N₂O's reactivity is warranted for broader applications.