Studies on Fluorinated Vinylic and Aromatic Alcohols and Esters

Abstract

Synthetic studies and pK a measurements are reported on a number of highly fluorinated tertiary alcohols and diols, namely (CF 2 CF)C(CF 3 ) 2 OH, (CF 2 CF) 2 C(CF 3 )OH, (C 6 F 5 )C(CF 3 ) 2 OH, (C 6 F 5 ) 2 C(CF 3 )OH, (C 6 F 5 ) 3 COH, (C 6 H 5 )C(CF 3 ) 2 OH, [(CF 3 ) 2 COH] 2 , and [(C 6 F 5 )C(CF 3 )OH] 2 . General agreement is found with earlier work reporting a correlation between pK a values and differences between free and H-bonded O—H stretching frequencies.The reaction of C 6 F 5 Li with the acyl halides CF 3 COCl and C 6 F 5 COCl in appropriate molar ratio gives the esters (C 6 F 5 ) 2 C(CF 3 )OCOC 6 F 5 and (C 6 F 5 ) 3 COCOC 6 F 5 , respectively; this constitutes a useful preparative route to fully fluorinated esters.