On the mechanism of alcoholysis of allylic and benzylic alcohols and of epoxides in the presence of ceric ammonium nitrate

被引:15
作者
Chapuzet, JM [1 ]
Beauchemin, S [1 ]
Daoust, B [1 ]
Lessard, J [1 ]
机构
[1] UNIV SHERBROOKE,DEPT CHIM,CTR RECH ELECTROCHIM & ELECTROCATALYSE,SHERBROOKE,PQ J1K 2R1,CANADA
关键词
alcoholysis; allylic and benzylic alcohols; cerium IV;
D O I
10.1016/0040-4020(96)00076-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The methanolysis of allylic alcohols, benzylic tertiary alcohols and epoxides in the presence of a catalytic amount of eerie ammonium nitrate (CAN) is shown to be catalysed by protons generated from the oxidation of methanol. This reaction is also catalysed by Lewis acids.
引用
收藏
页码:4175 / 4180
页数:6
相关论文
共 7 条
[1]  
BRANDRUP J, 1989, POLYM HDB
[2]  
Fieser L. F., 1961, ADV ORGANIC CHEM
[3]   CERIUM(IV), AS A SELECTIVE AND EFFICIENT CATALYST FOR ALCOHOLYSES OF ALLYLIC AND TERTIARY BENZYLIC ALCOHOLS [J].
IRANPOOR, N ;
MOTHAGHINEGHAD, E .
TETRAHEDRON, 1994, 50 (06) :1859-1870
[4]   MILD, EFFICIENT AND SELECTIVE OPENING OF EPOXIDES WITH ALCOHOLS CATALYZED BY CERIC(IV) AMMONIUM-NITRATE [J].
IRANPOOR, N ;
BALTORK, IM .
SYNTHETIC COMMUNICATIONS, 1990, 20 (18) :2789-2797
[5]   2,3-DICHLORO-5,6-DICYANO-PARA-BENZOQUINONE, AN EFFICIENT, MILD, NEUTRAL AND HIGHLY REGIOSELECTIVE CATALYST FOR ALCOHOLYSIS OF EPOXIDES [J].
IRANPOOR, N ;
BALTORK, IM .
TETRAHEDRON LETTERS, 1990, 31 (05) :735-738
[6]  
IRANPOOR N, 1994, SYNTHESIS-STUTTGART, P1152
[7]  
VIET MTP, 1979, THESIS U SHERBROOKE