Studies on Fluorinated Vinylic and Aromatic Alcohols and Esters
- 15 February 1972
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 50 (4) , 512-520
- https://doi.org/10.1139/v72-079
Abstract
Synthetic studies and pKa measurements are reported on a number of highly fluorinated tertiary alcohols and diols, namely (CF2CF)C(CF3)2OH, (CF2CF)2C(CF3)OH, (C6F5)C(CF3)2OH, (C6F5)2C(CF3)OH, (C6F5)3COH, (C6H5)C(CF3)2OH, [(CF3)2COH]2, and [(C6F5)C(CF3)OH]2. General agreement is found with earlier work reporting a correlation between pKa values and differences between free and H-bonded O—H stretching frequencies.The reaction of C6F5Li with the acyl halides CF3COCl and C6F5COCl in appropriate molar ratio gives the esters (C6F5)2C(CF3)OCOC6F5 and (C6F5)3COCOC6F5, respectively; this constitutes a useful preparative route to fully fluorinated esters.Keywords
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