Mechanistic aspects of superacid mediated condensation of polyphenols with ketones. Implications for polymer synthesis.

A detailed computational study of possible reaction paths for methanesulfonic and triflic acid mediated polyhydroxyalkylation reaction between resorcinol and trifluoracetone accompanied by cyclodehydration to give 9H-xanthene containing polymers has been carried out at M06-2X/6-311+G level of theory. A cluster solvation model was used for the calculations. The calculations revealed that the most kinetically favorable reaction path involves the cyclodehydration occurring during the polymer forming step.