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.
View MoreWENZHOU M&C FOREIGN TRADE CO.,LTD.
Contact:+86-577-88862917
Address:No.8 Liming West Road,Wenzhou,zhejiang,China
Shuanghe Bio-Technology Limited(expird)
Contact:+86-571-61710758,18968016640
Address:Jinqiao north road 916# Fuyang
Contact:13120882795；+86-21-34621078;+86-021-31122318
Address:Suite 2,No.2715 Longwu Road
Weifang Arylchem Chemical Co., LTD
Contact:86-536-5217866
Address:Development Zone, Shouguang, Shandong Province
Kunshan Yalong Trading Co,.Ltd
Contact:86-512-57621185
Address:805-807 Room Hongqiao Mansion ,1088 West Qianjin Road, Kunshan, Jiangsu，China
Doi:10.1021/jo00001a077
(1991)Doi:10.1016/0031-9422(90)85174-E
(1990)Doi:10.1021/jm300603y
(2012)Doi:10.1055/s-0030-1258451
(2011)Doi:10.1002/prac.19983400110
(1998)Doi:10.1007/BF00962396
(1990)
