Acyl trifluoroacetates. Part III. Trifluoroacetylation of hydroxy-groups with acetyl trifluoroacetate

Abstract

Kinetic and product composition studies have been made on the simultaneous acetylation and trifluoroacetylation of hydroxy-compounds by acetyl trifluoroacetate in carbon tetrachloride in the presence of certain pyridine bases. The marked change of reaction of p-chlorophenol from acetylation to trifluoroacetylation in the presence of base in contrast to the insensitivity of propan-2-ol is interpreted as a dependence on the extent of hydrogen-bonding of substrate with base. Solvation of the acetate leaving-group may be an important factor in the tifluoroacetic acid-catalysed reaction of propan-2-ol with acetyl trifluoroacetate.