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Related Concept Videos

Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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...
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

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.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 para position.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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, or cyano...

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Updated: May 27, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

A 1,3-dihydro-1,3-azaborine debuts.

Senmiao Xu1, Lev N Zakharov, Shih-Yuan Liu

  • 1Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA.

Journal of the American Chemical Society
|November 19, 2011
PubMed
Summary

Researchers synthesized and characterized 1,3-dihydro-1,3-azaborine, a stable aromatic compound and BN isostere of benzene. This discovery expands chemical diversity for applications in medicine and materials science.

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Medicinal Chemistry

Background:

  • Benzene is a fundamental aromatic building block in chemistry.
  • Developing novel aromatic systems with unique electronic properties is crucial for advancing science.
  • Boron-nitrogen (BN) isosterism offers a pathway to modify aromatic ring systems.

Purpose of the Study:

  • To report the first synthesis and characterization of 1,3-dihydro-1,3-azaborine.
  • To investigate the aromatic character and reactivity of this novel BN heterocycle.
  • To expand the chemical space of arenes through BN/CC isosterism.

Main Methods:

  • Chemical synthesis of 1,3-dihydro-1,3-azaborine.
  • Single crystal X-ray diffraction for structural analysis.

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

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  • Investigation of reaction chemistry, including nucleophilic and electrophilic substitutions.

    • Main Results:

    • Successful synthesis and characterization of 1,3-dihydro-1,3-azaborine.
    • Structural analysis confirms significant aromatic character and electron delocalization.
    • Demonstrated reactivity through nucleophilic substitution at boron and electrophilic aromatic substitution.

    Conclusions:

    • 1,3-Dihydro-1,3-azaborine is a stable, aromatic BN heterocycle.
    • This compound exhibits versatile reactivity, similar to benzene derivatives.
    • The study introduces a new class of arene isosteres with potential applications in biomedicine and materials science.