Intramolecular general-acid and electrostatic catalysis in acetal hydrolysis. Hydrolysis of 2-(substituted phenoxy)-6-carboxytetrahydropyrans and 2-alkoxy-6- …

TH Fife, SH Jaffe, R Natarajan

Index: Fife, Thomas H.; Jaffe, Stuart H.; Natarajan Journal of the American Chemical Society, 1991 , vol. 113, # 20 p. 7646 - 7653

Full Text: HTML

Citation Number: 13

Abstract

Abstract: Rate constants have been determined for hydrolysis of a series of trans-2- (substituted phenoxy)-6-carboxytetra-hydropyrans (e, a) in H20 and 50% dioxane-H20. The second-order rate constant (k2) for the apparent hydronium ion catalyzed reaction of the anionic species of the pnitro derivative in 50% dioxane-H20 (50 “C) is 620-fold larger than the second-order rate constant for hydrolysis of 2-(pnitrophenoxy) tetrahydropyran. The ...