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Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

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Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal, such as sodium,...
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Preparation of Amides01:29

Preparation of Amides

3.9K
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...
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Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.3K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
4.3K
Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

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The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
4.4K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.9K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

5.3K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
5.3K

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Preparation of Binary and Ternary Deep Eutectic Systems
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Assessing Sodium Amide Reagents for Ester Amidations in Deep Eutectic Solvents in Continuous Flow.

Andrew W J Platten1, Bruno Pinho2, Laura Torrente-Murciano2

  • 1Department für Chemie Biochemie und Pharmazie, Universität Bern, Freiestrasse 3, 3012 Bern, Switzerland.

ACS Sustainable Chemistry & Engineering
|November 14, 2025
PubMed
Summary

This study introduces sodium amides in deep eutectic solvents (DES) for efficient ester and C-F bond amidation under mild conditions. This novel approach in continuous flow chemistry enhances reactivity and prevents reactor clogging by dispersing byproducts.

Keywords:
Deep Eutectic Solventscontinuous flowsodium amidessolvent effectssustainable organometallic reagents

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Area of Science:

  • Organic Synthesis
  • Flow Chemistry
  • Green Chemistry

Background:

  • Sodium amide chemistry traditionally requires anhydrous conditions and is limited in synthetic scope.
  • Deep eutectic solvents (DES) offer unique properties for facilitating chemical reactions.

Purpose of the Study:

  • To explore the use of sodium amides in DES for efficient amidation reactions.
  • To develop a continuous flow process for amidation using sodium amides in DES.
  • To investigate the role of DES in enhancing reactivity and managing byproducts.

Main Methods:

  • Amidation of esters and C-F bond amination of difluoropyridine using sodium amides in DES.
  • Continuous flow reactor setup operating at room temperature.
  • In situ synthesis of sodium amide reagents.
  • X-ray crystallography and spectroscopic studies to characterize reagents.

Main Results:

  • Efficient amidation of esters and C-F bonds achieved at room temperature, tolerating air and moisture.
  • DES facilitates a biphasic system enabling segmented flow and preventing reactor clogging by dispersing byproducts.
  • Higher conversions and selectivities observed compared to conventional batch conditions.
  • In situ synthesis of sodium amides demonstrated using NaN-(SiMe3)2.
  • Characterization revealed monomeric/dimeric species of sodium amides in THF.

Conclusions:

  • Sodium amides in DES represent a powerful and versatile tool for amidation in continuous flow.
  • This method offers a greener and more efficient alternative to traditional amidation techniques.
  • The unique properties of DES are crucial for the success of this flow chemistry approach.