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

Perfluorinated tetrathiacalix[4]arene was obtained by heating perfluoro- -xylene with thiourea or 2,5-difluoro-4,6-bis(trifluoromethyl)benzene-1,3-dithiol at 90 °C. Interaction of perfluoro- -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- -xylene with resorcinol under heating with thiourea gives polyfluorinated oxathiacalixarenes containing six and five aromatic nuclei, respectively.