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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

1.8K
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.
1.8K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

1.9K
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...
1.9K
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

4.5K
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
4.5K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.1K
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...
3.1K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.0K
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,...
2.0K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

3.2K
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.
3.2K

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Updated: Apr 21, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Quinone diazides for olefin functionalization.

Hai T Dao1, Phil S Baran

  • 1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA).

Angewandte Chemie (International Ed. in English)
|November 5, 2014
PubMed
Summary
This summary is machine-generated.

Modern catalysis enables quinone diazides, classic diazo compounds, for olefin cyclopropanation reactions. This research unlocks their potential in organic synthesis and materials science applications.

Keywords:
olefin functionalizationquinone diazidesteroidstriazenes

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Area of Science:

  • Organic synthesis
  • Materials science
  • Catalysis

Background:

  • Quinone diazides are versatile organic compounds with documented utility in materials science.
  • Their application in synthetic organic chemistry has been historically limited.
  • Classic diazo compounds offer unique reactivity profiles.

Purpose of the Study:

  • To explore the application of quinone diazides in modern organic synthesis.
  • To demonstrate the utility of catalytic methods with quinone diazides.
  • To enable inter- and intramolecular olefin cyclopropanation reactions using quinone diazides.

Main Methods:

  • Utilizing modern catalytic tools with free quinone diazides.
  • Employing suitably masked quinone diazides in synthetic transformations.
  • Investigating both intermolecular and intramolecular cyclopropanation reactions.

Main Results:

  • Successfully employed catalytic methods with quinone diazides.
  • Achieved efficient inter- and intramolecular olefin cyclopropanation.
  • Unleashed the synthetic potential of these diazo compounds.

Conclusions:

  • Modern catalysis provides a powerful approach to utilize quinone diazides in organic synthesis.
  • Quinone diazides can be effectively employed in olefin cyclopropanation reactions.
  • This work expands the synthetic utility of quinone diazides for creating complex molecular architectures.