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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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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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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.8K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.8K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

18.6K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
18.6K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

10.4K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

7.9K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
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Cone p-aminocalix[4]arenes enriched with 'clickable' alkyne or azide functionalities.

Ilia Korniltsev1, Vasily Bazhenov1, Alexander Gorbunov1

  • 1Department of Chemistry, M. V. Lomonosov Moscow State University, Lenin's Hills 1, 119991 Moscow, Russia.

Beilstein Journal of Organic Chemistry
|March 18, 2026
PubMed
Summary

New methods synthesize multifunctional calixarenes with amino and clickable groups. These platforms enable the creation of complex supramolecular assemblies and advanced macrocyclic structures.

Keywords:
calixarene aminesdimeric capsulesfunctionalizationtetraureacalixarenestriazoles

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Macrocyclic Chemistry

Background:

  • Calixarenes are versatile macrocyclic hosts with tunable properties.
  • Functionalization of calixarene rims is key to developing advanced materials.
  • Click chemistry offers efficient methods for molecular assembly.

Purpose of the Study:

  • To develop efficient synthetic routes for heteromultifunctional calix[4]arenes.
  • To create calixarene platforms with both amino and clickable functionalities (alkyne or azide).
  • To demonstrate the utility of these platforms in synthesizing complex supramolecular structures.

Main Methods:

  • Synthesis of propargylated and 2-azidoethylated p-aminocalix[4]arenes using multi-step strategies.
  • Protection of amino groups as tert-butoxycarbonyl (Boc) derivatives for purification and transformation.
  • Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) 'click' reactions for triazole formation.
  • Subsequent functionalization of amino groups to form tetraureacalix[4]arenes.

Main Results:

  • Successfully synthesized five types of multifunctional calix[4]arenes with diverse functional groups.
  • Demonstrated efficient 'click' reactions to form triazolated macrocycles.
  • Obtained narrow-rim triazolated tetraureacalix[4]arenes, showing potential for capsule formation.
  • Confirmed that triazole groups do not hinder the formation of supramolecular capsules.

Conclusions:

  • The developed p-aminocalix[4]arenes serve as versatile platforms for further functionalization.
  • These platforms facilitate the synthesis of sophisticated supramolecular assemblies with tailored properties.
  • The combination of amine reactivity and click chemistry provides a powerful toolkit for macrocycle design.