ACID-CATALYZED AND MERCURIC ION CATALYZED HYDROLYSIS OF 2-(PARA-SUBSTITUTED PHENYL)-1,3-OXATHIOLANES

The hydrolysis of 2-(para-substituted phenyl)-!,3-oxathiolanes to give para-substituted benzaldehydes and mercaptoethanol is hydronium ion catalyzed and mercuric ion catalyzed. Mercuric ion catalysis is from 300 to 1600 times more efficient than hydronium ion catalysis. For the acid-catalyzed reactions, ρ = -1.66, ΔS± = – 17.8 eu, and the deuterium solvent kinetic isotope effect kD/kH = 2.15, results consistent with an A2 mechanism involving solvent water in the transition state. © 1968, American Chemical Society. All rights reserved.