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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...

Structural Isomerism

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...

Coordination Compounds and Nomenclature

Coordination Compounds and Nomenclature

In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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.

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...

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Related Experiment Video

Updated: Jun 28, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

Azophosphines: Synthesis, Structure and Coordination Chemistry.

Emma J Jordan¹, Ethan D E Calder¹, Holly V Adcock¹

¹School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|April 16, 2024

Summary

This summary is machine-generated.

Researchers synthesized and characterized novel phosphorus-containing azophosphines. These compounds, unlike their nitrogen counterparts, show potential as versatile ligands in ruthenium complexes, offering controlled monodentate or bidentate coordination.

Keywords:

Azophosphines Coordination Chemistry Ligands Main-group Chemistry Phosphorus

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Last Updated: Jun 28, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

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Published on: November 22, 2016

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Published on: May 12, 2023

Area of Science:

Organophosphorus chemistry
Coordination chemistry
Ligand design

Background:

Nitrogen in organic functional groups can be replaced by phosphorus to unlock novel properties.
Phosphorus analogues of triazenes, known as azophosphines, are underexplored but promising as ligands.
Small bite-angle ligands are valuable in coordination chemistry for controlling metal complex structures and reactivity.

Purpose of the Study:

To synthesize and characterize air-stable azophosphine-borane complexes.
To deprotect these complexes to obtain free azophosphines.
To investigate the coordination behavior of azophosphines as ligands in metal complexes.

Main Methods:

Synthesis of azophosphine-borane complexes.
Deprotection reactions to yield free azophosphines.
Structural characterization using experimental (e.g., X-ray crystallography) and computational methods.
Coordination studies with ruthenium precursors.

Main Results:

A family of air-stable azophosphine-borane complexes was successfully synthesized.
Azophosphines were obtained and structurally characterized, revealing available phosphorus lone pairs for coordination.
Neutral azophosphines demonstrated utility as ligands in ruthenium complexes.
Controlled monodentate and bidentate coordination modes were observed, contrasting with nitrogen analogues.

Conclusions:

Azophosphines represent a viable alternative to traditional nitrogen-based ligands.
The unique electronic and steric properties of azophosphines enable controlled coordination in metal complexes.
This work expands the scope of phosphorus-containing ligands for applications in catalysis and materials science.