Journal of the Chemical Society. Perkin transactions II p. 965 - 970 (1990)
Update date:2022-08-02
Topics:
Longridge, Jethro L.
Nicholson, Stuart
The kinetics of hydrolysis of (5Z)-7-(<2RS,4RS,5SR>-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.
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