Micellar media for the efficient ring opening of epoxides with CN-, N3-, NO3-,NO2-, SCN-, Cl- and Br- catalyzed with Ce(OTf)4

被引：72
作者：
Iranpoor, N [1 ]
Firouzabadi, H
Shekarize, M
机构：
[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran
[2] Res Inst Petr Ind, Addit Dept, Chem & Petrochem Div, Tehran, Iran
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2003年 / 1卷 / 04期
关键词：
D O I：
10.1039/b211697a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Micellar media are introduced for the efficient ring opening of epoxides with sodium salts of nucleophiles such as CN-, N-3(-), NO3-, NO2-, SCN-, Br- and Cl-, catalyzed with Ce(OTf)(4). This method is an efficient procedure for the synthesis of different beta-substituted alcohols under mild reaction conditions. The reaction with SCN- is an easy procedure for the high yielding preparation of epoxy sulfides.
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页码：724 / 727
页数：4
相关论文
共 60 条
[1]   CORRELATIONS BETWEEN SOLVENT POLARITY SCALES AND ELECTRON-TRANSFER KINETICS AND AN APPLICATION TO MICELLAR MEDIA [J].
ABBOTT, AP ;
MIAW, CL ;
RUSLING, JF .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1992, 327 (1-2) :31-46
[2]   XAS STUDY OF SOLUBILIZATION LOCI OF BROMINATED MOLECULES IN AQUEOUS MICELLAR SOLUTIONS [J].
ASCONE, I ;
DANGELO, P ;
PAVEL, NV .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (11) :2982-2990
[3]   A HIGHLY REGIOSELECTIVE CONVERSION OF EPOXIDES TO HALOHYDRINS BY LITHIUM HALIDES [J].
BAJWA, JS ;
ANDERSON, RC .
TETRAHEDRON LETTERS, 1991, 32 (26) :3021-3024
[4]   COPOLYMERIZATION OF ACRYLAMIDE AND A HYDROPHOBIC MONOMER IN AN AQUEOUS MICELLAR MEDIUM - EFFECT OF THE SURFACTANT ON THE COPOLYMER MICROSTRUCTURE [J].
BIGGS, S ;
HILL, A ;
SELB, J ;
CANDAU, F .
JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (03) :1505-1511
[5]   REGIOSELECTIVE AND CHEMOSELECTIVE SYNTHESIS OF HALOHYDRINS BY CLEAVAGE OF OXIRANES WITH METAL-HALIDES [J].
BONINI, C ;
RIGHI, G .
SYNTHESIS-STUTTGART, 1994, (03) :225-238
[6]   MICELLAR CATALYSIS OF ORGANIC-REACTIONS .29. SNAR REACTIONS WITH NEUTRAL NUCLEOPHILES [J].
BROXTON, TJ ;
MARCOU, V .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1041-1044
[7]   MICELLAR CATALYSIS OF ORGANIC-REACTIONS .31. A STUDY OF THE EFFECTS OF MICELLES OF CETYLTRIMETHYLAMMONIUM BROMIDE ON SOME SNAR REACTIONS IN AQUEOUS BINARY-MIXTURES [J].
BROXTON, TJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (05) :667-676
[8]   ABNORMALLY HIGH NUCLEOPHILICITY OF MICELLAR-BOUND AZIDE ION [J].
BUNTON, CA ;
MOFFATT, JR ;
RODENAS, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (09) :2653-2655
[9]   ION BINDING AND REACTIVITY AT CHARGED AQUEOUS INTERFACES [J].
BUNTON, CA ;
NOME, F ;
QUINA, FH ;
ROMSTED, LS .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (12) :357-364
[10]  
BUNTON CA, 1971, TETRAHEDRON LETT, P121
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