Journal of Organic Chemistry p. 1116 - 1123 (1989)
Update date:2022-09-26
Topics:
Onaka, Makoto
Sugita, Keisuke
Izumi, Yusuke
Sodium azide is supported on three types of porous solid acids (zeolite, alumina, and silica gel) and applied to several reactions with epoxides.A systematic investigation reveals that the reactivities of the supported reagents are greatly influenced by loading amounts of NaN3, amounts of adsorbed water in the reagents, acidic properties of the solid acids, and reaction solvents.For demonstrating the utility of supported NaN3 reagents in selective organic syntheses, nucleophilic ring-opening reactions of 2,3-epoxy alcohols with the supported reagents are examined.Among the supported reagents, only the Ca2+-exchanged zeolite-supported reagent induces a C-3 ring opening in a highly regioselective manner (>90percent).It is deduced that the role of calcium ions in the zeolite is to increase the acid strength of the zeolite facilitating the ring cleavage of epoxides and to fix the conformation of epoxy alcohols through forming chelate complexes with calcium ions.
View MoreLanzhou huibang biological chemical technology Co., LTD
Contact:0931-7843964
Address:NO.2011,Yannan Road,Chengguan,
Daqing New Century Fine Chemical Co., Ltd.(expird)
Contact:010-57126694
Address:No.39, jinxing cun, honggang district
Zhejiang Newfine Industry Co.,Ltd.
Contact:+86-573-82262042
Address:No.225,Dongqing Road, garoms@163.com
Contact:+86-10-62651721
Address:29 Yongxing Road, Daxing District,Beijing China
Shanghai PotentPharm Science and Technology Co.,Ltd
Contact:86-021-51969655
Address:Unit B, Building 18, No.300, Chuantu Rd,Pudong District, Shanghai 201202, China
Doi:10.1016/S0040-4039(01)82114-6
(1981)Doi:10.1246/bcsj.61.141
(1988)Doi:10.1021/ja00194a040
(1989)Doi:10.1007/BF00633183
(1988)Doi:10.1016/0008-6215(88)84136-3
(1988)Doi:10.1016/S0040-4039(00)80403-7
(1988)