CERIC AMMONIUM-NITRATE, AN EFFICIENT CATALYST FOR MILD AND SELECTIVE OPENING OF EPOXIDES IN THE PRESENCE OF WATER THIOLS AND ACETIC-ACID

被引:97
作者
IRANPOOR, N
BALTORK, IM
ZARDALOO, FS
机构
[1] Department of Chemistry, Shiraz University Shiraz
关键词
D O I
10.1016/S0040-4020(01)80723-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ring opening of epoxides with catalytic amounts of Ce(IV) as ceric ammonium nitrate (CAN) are performed efficiently in the presence of water, Thiols and acetic acid under mild conditions. The epoxides are opened with high regio-and stereoselectivity and with good to excellent yields. The products formed from the reaction of polar substituted epoxides in acetic acid were found to be derivative of succinic acid diester. The mechanism of the reaction is believed to be a radical type, involving the formation of an epoxonium radical cation.
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页码:9861 / 9866
页数:6
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