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Synthesis of Calix

Chowdhury1, Bridson, Georghiou

  • 1Department of Chemistry and X-ray Crystallography Unit, Memorial University of Newfoundland, St. John's, Newfoundland A1B 3X7, Canada.

The Journal of Organic Chemistry
|June 8, 2000
PubMed
Summary

Researchers synthesized p-tert-butylcalix[4]arene triflates and explored their reactions. A novel benzophenone clathrate (6) was formed, with its X-ray crystal structure reported for the first time.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Crystal Engineering

Background:

  • Calix[4]arene derivatives are versatile macrocyclic hosts.
  • Triflates of calix[4]arenes are key intermediates in organic synthesis.
  • Palladium-catalyzed reactions offer efficient synthetic routes.

Purpose of the Study:

  • To synthesize and characterize various p-tert-butylcalix[4]arene triflates.
  • To investigate the reactivity of these triflates under palladium-catalyzed conditions.
  • To explore the formation and structural characterization of novel clathrate complexes.

Main Methods:

  • Synthesis of p-tert-butylcalix[4]arene mono-, bis-, tris-, and tetrakistriflates.
  • Palladium-catalyzed carbonylative coupling reactions.
  • Suzuki-Miyaura coupling and deoxygenation reactions.
  • X-ray crystallography for structural determination.

Main Results:

  • Formation of p-tert-butylcalix[4]arene triflates (3, 2, 4, 5) achieved.
  • A novel 1:1 clathrate (6) of benzophenone and calixarene derivative 3 was synthesized.
  • The first nonsolvent-derived clathrate of a calix[4]arene derivative was structurally characterized by X-ray crystallography.
  • A triethylamine clathrate with 3 was observed during deoxygenation.

Conclusions:

  • The study successfully synthesized and characterized novel calixarene triflates.
  • The formation and structural elucidation of a unique nonsolvent-derived benzophenone clathrate demonstrate new supramolecular assembly possibilities.
  • Palladium-catalyzed reactions provide effective pathways for functionalizing calix[4]arenes and forming inclusion complexes.

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