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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

3.7K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
3.7K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.8K
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...
3.8K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.7K
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.
2.7K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

3.2K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.2K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

2.7K
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.
2.7K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

3.2K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
3.2K

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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Aliphatic Amines Unlocked for Selective Transformations through Diazotization.

Jakub Durka1, Barbara Zielińska1,2, Dorota Gryko1

  • 1Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.

Angewandte Chemie (International Ed. in English)
|December 2, 2024
PubMed
Summary

Aliphatic amine diazotization is now controllable using isopentyl nitrite in HFIP, enabling new synthetic routes. This breakthrough allows electrophilic aromatic substitution and carbocation generation from abundant alkyl reagents.

Keywords:
Aliphatic aminesAlkylationDiazotizationSynthetic methods

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Diazonium ions from aromatic amines are vital synthetic reagents.
  • Diazonium ions from aliphatic amines are typically unstable and lead to complex product mixtures, limiting their synthetic utility.

Purpose of the Study:

  • To overcome the limitations of aliphatic amine diazotization.
  • To develop a controlled method for generating and utilizing diazonium ions from aliphatic amines.

Main Methods:

  • Utilizing isopentyl nitrite as a diazotizing agent.
  • Performing the reaction in hexafluoroisopropanol (HFIP) solvent.

Main Results:

  • Achieved controlled diazotization of aliphatic amines.
  • Enabled electrophilic aromatic substitution reactions using aliphatic amine-derived diazonium ions.
  • Demonstrated the transformation of aliphatic amines into valuable synthetic building blocks.
  • Showcased the potential for using demanding substrates like amino acids.

Conclusions:

  • The developed methodology provides a reliable method for aliphatic amine diazotization.
  • This approach expands the synthetic utility of abundant aliphatic amines and amino acids.
  • The new method opens avenues for generating carbocations and accessing diverse chemical space.