R. Filler, William K. Gnandt, Wei Chen
Apr 1, 1991
Citations
0
Influential Citations
8
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract 1,3,5-Tris(trifluoromethyl)benzene reacts with n-butyllithium and carbon dioxide to give a high yield of 2,4,6-tris(trifluoromethyl)benzoic acid. The acid has been well characterized by spectral and pK a data. The acid chloride is formed only slowly under stringent conditions. The acid fails to undergo normal esterification with ethanol because of steric hindrance to the required tetrahedral intermediate. The ester does form via the linear acylium ion. A highly substituted phenolic ester of the acid has been obtained via a mixed anhydride. Attempts to prepare the corresponding acetophenone and a related vinyl ketone are described.