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

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

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...

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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.

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

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

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.

Diazonium Group Substitution: –OH and –H

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.

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

Preparation of 1° Amines: Azide Synthesis

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...

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Related Experiment Video

Updated: Jul 13, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

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Published on: August 22, 2018

Synthesis of Complex Diarylamines through a Ring-Opening Difunctionalization Strategy.

Erika Linde¹, Berit Olofsson¹

¹Department of Organic Chemistry Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden.

Angewandte Chemie (International Ed. in English)

|October 17, 2023

Summary

This study introduces a novel method for synthesizing diverse diarylamines from cyclic amines, crucial for drug discovery. The efficient one-pot reaction allows for broad functionalization and late-stage modifications of complex molecules.

Keywords:

Amines Arylations Difunctionalizations Hypervalent Compounds Ring-Openings

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Published on: August 22, 2018

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Area of Science:

Organic Chemistry
Medicinal Chemistry

Background:

Cyclic amines are vital scaffolds in drug discovery.
Expanding their properties is key to developing new therapeutics.

Purpose of the Study:

To develop a novel synthetic strategy for diarylamines.
To enable skeletal diversification of cyclic amines for drug discovery applications.

Main Methods:

Diarylation and skeletal diversification of unstrained cyclic amines.
Synthesis of amino-substituted diaryliodonium salts.
Atom-efficient one-pot N-arylation/ring opening with nucleophiles.

Main Results:

A wide variety of highly functionalized diarylamines were synthesized.
The method demonstrated high functional group tolerance with over 20 nucleophiles.
Efficient late-stage functionalization of natural products and pharmaceuticals was achieved.

Conclusions:

The developed method provides access to diverse diarylamines with potential in drug discovery.
The strategy is versatile, enabling modifications of complex molecules and pharmaceuticals.