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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
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Preparation of Alkynes: Dehydrohalogenation02:34

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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.
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Preparation of Alkynes: Alkylation Reaction02:27

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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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Cycloaddition Reactions: Overview01:16

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the...
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Updated: Sep 11, 2025

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Synthesis of Monothiacalix[4]arene Using the Fragment Condensation Approach.

Daniel Kortus1, Oliver Moravec1, Hynek Varga1

  • 1Department of Organic Chemistry, University of Chemistry and Technology Prague (UCTP), Technická 5, 166 28 Prague, Czech Republic.

Molecules (Basel, Switzerland)
|August 14, 2025
PubMed
Summary

A new method for preparing mixed-bridged (CH2 and S) calix[4]arenes offers high yields. Variable-temperature NMR studies reveal insights into the dynamic behavior and hydrogen bonding in these macrocycles.

Keywords:
bisphenolscalixareneconformationflip-flop mechanismfragment condensationmacrocyclizationsynthesisthiacalixarenevariable temperature NMR

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Macrocyclic Chemistry

Background:

  • Calix[4]arenes are versatile macrocyclic platforms.
  • Mixed-bridged calix[4]arenes incorporating sulfur present unique structural and dynamic properties.
  • Understanding the conformational dynamics is crucial for designing functional macrocycles.

Purpose of the Study:

  • To develop a simple and scalable synthesis for 2-monothiacalix[4]arene.
  • To investigate the dynamic behavior of the synthesized macrocycle and its oxidized derivative.
  • To elucidate the influence of sulfur incorporation and oxidation on macrocyclic conformation and hydrogen bonding.

Main Methods:

  • Synthesis via condensation of linear bisphenols.
  • Variable-temperature Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Computational analysis of dynamic processes (cone-cone inversion, flip-flop mechanism).

Main Results:

  • Successful preparation of 2-monothiacalix[4]arene (7) in high yield using two alternative routes.
  • Determination of the cone-cone equilibrium and inversion barriers for compound 7 (ΔG‡ = 63 kJ·mol⁻¹) and its sulfone derivative 14 (ΔG‡ = 60 kJ·mol⁻¹).
  • Quantification of barriers for the flip-flop hydrogen bond mechanism at low temperatures (ΔG‡ = 44 kJ·mol⁻¹ for 7 vs. ΔG‡ = 40 kJ·mol⁻¹ for 14), indicating weakened hydrogen bonds in the sulfone.

Conclusions:

  • The developed synthetic strategy is efficient for producing mixed-bridged calix[4]arenes.
  • Sulfur incorporation and oxidation influence the conformational dynamics and hydrogen bonding within the calixarene framework.
  • The findings provide valuable insights into the structure-property relationships of sulfur-containing macrocycles.