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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...
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.9K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
3.9K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

2.4K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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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
Physical Properties of Amines01:26

Physical Properties of Amines

3.2K
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
3.2K
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

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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Azaphosphinines and their derivatives.

J Nolan McNeill1, Jeremy P Bard2, Darren W Johnson1

  • 1Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, OR 97403-1253, USA. haley@uoregon.edu.

Chemical Society Reviews
|November 24, 2023
PubMed
Summary
This summary is machine-generated.

Azaphosphinines, six-membered heterocycles with phosphorus and nitrogen, are gaining attention. This review covers the synthesis and diverse applications of all six isomers, particularly PV-oxo forms.

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Area of Science:

  • Heterocyclic Chemistry
  • Organophosphorus Chemistry
  • Materials Science

Background:

  • Azaphosphinines, six-membered rings with one phosphorus and one nitrogen atom, are uncommon heterocyclic scaffolds.
  • Despite a long history, recent research shows a surge in publications on azaphosphinine chemistry.
  • These compounds exist in six isomers, varying in pnictogen orientation and phosphorus valence (PIII vs. PV).

Purpose of the Study:

  • To provide a comprehensive overview of the synthesis and applications of all six azaphosphinine isomers.
  • To highlight the growing importance and diverse utility of this heterocyclic system.
  • To focus on PV-oxo azaphosphinines, which are frequently formed or oxidized to this state.

Main Methods:

  • Literature review synthesizing recent advancements in azaphosphinine chemistry.
  • Categorization of synthesis strategies for different azaphosphinine isomers.
  • Compilation of reported applications across various chemical disciplines.

Main Results:

  • Detailed exploration of synthetic routes leading to diverse azaphosphinine structures.
  • Demonstration of PV-oxo azaphosphinines as a prevalent and significant subclass.
  • Emerging applications in asymmetric catalysis, supramolecular chemistry, cellular imaging, and medicinal chemistry.

Conclusions:

  • Azaphosphinines represent a versatile class of heterocycles with expanding synthetic accessibility.
  • Their unique structural features enable a broad spectrum of applications in modern chemistry.
  • Continued research promises further innovation in azaphosphinine-based materials and technologies.