M. Lajunen et al., Acid-catalyzed hydrolysis of bridged bi- and tricyclic compounds. XXXVII. Kinetics and mechanisms of 1- and 3-acetoxynortricyclanes, J PHYS ORG, 13(2), 2000, pp. 133-138
The disappearance of 3- and 1-acetoxynortricyclanes (1 and 2) in aqueous pe
rchloric acid was followed by capillary gas chromatography at different tem
peratures and acid concentrations. According to the activation parameters,
solvent deuterium isotope effects and parameters of excess acidity equation
s, the A(AC)2 ester hydrolysis with two water molecules in the transition s
tate is dominant at the lower acid concentrations studied (1-5.5 M HClO4) a
nd the Ad(E)2 hydration of the cyclopropane ring is dominant at higher acid
concentrations (6-8 M HClO4) at 298 K, 3-Nortricyclanol (3) is formed via
hydrolysis from 1, whose hydration products were not analyzed. 2-Norbornano
ne (3) is formed via both hydrolysis and hydration from 2. Copyright (C) 20
00 John Wiley & Sons, Ltd.