Structure Determination of Perfluoro-1-methylcyclohexanol, HOC(CF3)(C5F10), and Perfluorocyclohexanol, HOC(F)(C5F10), in the Solid and Gaseous Phases

• Applicants: Professor Dr. Ingo Krossing; Professor Dr. Norbert W. Mitzel
• Subject Area: Inorganic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2016 to 2018
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 323895747

• Final Report Year: 2018

Final Report Abstract

c-C6F10(CF3)OH (1) was obtained by protonation of its alkoxide [NMe4]+[C7F13O]− with conc. H2SO4. A similar attempt to prepare the α−fluoroalcohol undecafluorocyclohexanol (c-C6F11OH, 2) failed. However, the thermally unstable 2 was prepared by addition of hydrogen fluoride to the corresponding ketone. Decafluorocyclohexane-1,1-diol (c-C6F10(OH)2) was prepared by acidic workup of the corresponding alkoxide [NMe4]+[C6F11O]− with sulfuric acid, which yielded (c-C6F10(OH)2) and fluorosulfonic acid. The structures of c-C6F10(CF3)OH (H2O adduct in the crystal) was elucidated by single-crystal X-ray and gas-phase electron-diffraction studies. The instability and high reactivity of 2 did not allow obtaining structural data. Instead, the structure of the diol c-C6F10(OH)2) was elucidated in the solid and gaseous phases.

Publications

• The perfluorinated alcohols c-C6F11OH, c-C6F10-1,1-(OH)2 and c-C6F10-1-(CF3)OH. Chemical Communications, 2018
  Jonas Schaab, Miriam Schwab, Daniel Kratzert, Jan Schwabedissen, Hans-Georg Stammler, Norbert W. Mitzel and Ingo Krossing