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Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

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...

Preparation of Amides

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

Nomenclature of Primary Amines

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.

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 Amines: Reductive Amination of Aldehydes and Ketones

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

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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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Novel primary phosphinecarboxamides derived from diamines.

Erica N Faria¹, Andrew R Jupp¹, Jose M Goicoechea¹

¹Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, UK. jose.goicoechea@chem.ox.ac.uk.

Dalton Transactions (Cambridge, England : 2003)

|May 5, 2021

Summary

Researchers synthesized novel N-functionalised phosphinecarboxamides using the 2-phosphaethynolate anion and diamines. These compounds can be further transformed into valuable secondary phosphines via phosphide anion intermediates.

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Published on: November 22, 2016

Area of Science:

Organophosphorus Chemistry
Synthetic Organic Chemistry

Background:

The 2-phosphaethynolate anion (PCO-) is a reactive species with potential for novel compound synthesis.
Functionalized phosphines are important building blocks in various chemical applications.

Purpose of the Study:

To synthesize N-functionalised phosphinecarboxamides.
To explore the reactivity of the 2-phosphaethynolate anion with diamines.
To develop a route to secondary phosphines.

Main Methods:

Reaction of the 2-phosphaethynolate anion with hydrazine, methylenediamine, and ethylenediamine in the presence of acid.
Deprotonation of the resulting neutral compounds to generate phosphide anions.
Reaction of phosphide anions with electrophiles.

Main Results:

Successful synthesis of N-functionalised phosphinecarboxamides.
Generation of phosphide anions from the neutral compounds.
Formation of secondary phosphines through reaction with electrophiles.

Conclusions:

The 2-phosphaethynolate anion is a versatile precursor for synthesizing functionalized phosphine derivatives.
A novel synthetic pathway to secondary phosphines has been established.
The described methodology offers a new route for organophosphorus compound preparation.