Evidence for general base catalysis in the reaction between the tris-p-methoxyphenylmethyl cation and water in aqueous solution at 25 °C

Abstract

Stopped flow measurements on the rate of disappearance of the tris-p-methoxyphenylmethyl cation show that a small accelerating effect is produced by the bases 1,4-diazabicyclo[2.2.2]octane (DABCO), trimethylamine, and triethylamine, just as observed by Ritchie in the case of the Malachite Green cation. The alternative possibility that the bases might act as nucleophiles in forming quaternary ammonium ions as intermediates seems unlikely.