129372-16-3Relevant academic research and scientific papers
The Alkaline Stability of (5Z)-7-(-4-o-Hydroxyphenyl-2-trifluoromethyl-1,3-dioxan-5-yl)hept-5-enoic acid, ICI 185282. A Remarkable Intramolecular Hydride Transfer from a Trifluoromethyl Substituted Carbon Atom
Longridge, Jethro L.,Nicholson, Stuart
, p. 965 - 970 (1990)
The kinetics of hydrolysis of (5Z)-7-(-4-o-hydroxyphenyl-2-trifluoromethyl-1,3-dioxan-5-yl)hept-5-enoic acid, ICI 185282 (1a), have been studied.At low pH the compound undergoes conventional acid-catalyzed hydrolysis of the dioxane ring.However, under alkaline conditions, a second reaction is observed.Studies by NMR show that this process involves a quite unexpected intramolecular hydride transfer from a carbon atom carrying a strongly electron-withdrawing trifluoromethyl substituent.Additional studies on closely related compounds are reported and a mechanism involving a ring-opened quinone methide intermediate is proposed.
