128886-78-2Relevant academic research and scientific papers
Stabilisation of the Thromboxane Ring System by Electron-withdrawing Substituents. Mechanism and Reactivity in the Hydrolysis of Alkyl and Aryl Oxetane Acetals.
Kirby, Anthony J.,Ryder, Hamish,Matassa, Victor
, p. 825 - 831 (2007/10/02)
Rates of acid-catalysed hydrolysis are reported as a function of pH for eleven oxetane acetals (6) in 20percent dioxane-water.The introduction of fluorine atoms into the 2-alkoxy group results in a 103-104-fold kinetic stabilisation, and the system is also stabilised by 2-aryl substituents.The pH-rate profiles for the two most reactive compounds (3b) and (12b) show that at low pH the reaction involves rapid conversion into the intermediate hemiacetal, followed by its rate-determining decomposition.For these compounds at pH > 6, and for all other oxetane acetals studied, the ring-opening step is rate determining.No general acid catalysis is apparent.
