Synthesis of Polyfluorinated Thia- and Oxathiacalixarenes Based on Perfluoro-<i>m</i>-xylene

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

• perfluorinated tetrathiacalix[4]arene
• perfluoro-<i>m</i>-xylene
• dioxadithiacalix[4]arenes
• tetraoxadithiacalix[6]arene
• thiourea
• 2,5-difluoro-4,6-bis(trifluoromethyl)benzene-1,3-dithiol