Preparation of Diols Containing Polyfluoro-1, 2-cycloalkylene Group and of Related Compounds

Abstract

Various diols, containing 3, 3, 4, 4-tetrafluoro-1, 2-cyclobutylene and 3, 3, 4, 4, 5, 5-hexafluoro1, 2-cyclopentylene group, HOIVIVCCH(CF2)HCCR3R4OH (n: 2 or 3;: H or CHs), have been synthesized by the addition reaction of alconols, e. g., methyl, ethyl, and isopropyl alcohol, with (polyfluorocyclobutenyl) or (polyfluorocyclopentenyl)alkanols under the irradiation of r-ray.
The apparent reactivity of alcohols observed in this addition reaction is in the following order:
C₂H₅0H> CH₃OH>(CH₂) ₂CHOH
The reverse was found for the effect of substituents in polyfluorocycloalkenes on the reactivity; and the reactivity of cycloalkenes having -C(CHs)20H group is the most and that of -those having -CH₂OH group is the least.
The (tetrafluorocyclobutenyl)alkanols are generally more reactive than the (hexafluorocyclopentenyl) alkanols.