Synthesis of Polyfluorinated Thia- and Oxathiacalixarenes Based on Perfluoro- m-xylene

Molecules. 2021 Jan 20;26(3):526. doi: 10.3390/molecules26030526.

Abstract

Perfluorinated tetrathiacalix[4]arene was obtained by heating perfluoro-m-xylene with thiourea or 2,5-difluoro-4,6-bis(trifluoromethyl)benzene-1,3-dithiol at 90 °C. Interaction of perfluoro-m-xylene with resorcinol or orcinol under mild conditions and subsequent heating of the mixture with 2,5-difluoro-4,6-bis(trifluoromethyl)benzene-1,3-dithiol leads to polyfluorinated dioxadithiacalix[4]arenes. Triphenyl and pentaphenyl ethers formed by the interaction of perfluoro-m-xylene with resorcinol under heating with thiourea gives polyfluorinated oxathiacalixarenes containing six and five aromatic nuclei, respectively.

Keywords: 2,5-difluoro-4,6-bis(trifluoromethyl)benzene-1,3-dithiol; X-ray analyses.; dioxadithiacalix[4]arenes; perfluorinated tetrathiacalix[4]arene; perfluoro-m-xylene; tetraoxadithiacalix[6]arene; thiourea.

MeSH terms

  • Benzene / chemistry*
  • Benzene Derivatives / chemistry*
  • Biodegradation, Environmental / drug effects
  • Calixarenes / chemical synthesis
  • Calixarenes / chemistry*
  • Fluorocarbons / chemistry
  • Phenols / chemical synthesis
  • Phenols / chemistry
  • Sulfides / chemical synthesis
  • Sulfides / chemistry
  • Toluene / analogs & derivatives
  • Toluene / chemistry
  • Xylenes / chemical synthesis
  • Xylenes / chemistry*

Substances

  • Benzene Derivatives
  • Fluorocarbons
  • Phenols
  • Sulfides
  • Xylenes
  • thiacalix(4)arene
  • Calixarenes
  • Toluene
  • Benzene
  • 3-xylene
  • dithiol
  • perfluoromethylcyclohexane