Isomerization of allylic alcohols to carbonyl compounds by aqueous-biphase rhodium catalysis

被引:48
作者
Bianchini, C [1 ]
Meli, A [1 ]
Oberhauser, W [1 ]
机构
[1] CNR, Ist Studio Stereochim & Energet Composti Coordina, I-50132 Florence, Italy
关键词
D O I
10.1039/b001478h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Isomerization of allylic and homoallylic alcohols is catalyzed by the zwitterionic Rh(I) complex (sulphos)Rh(cod) in water-n-octane to give the corresponding aldehyde or ketone in high yields and chemoselectivity. A pi -allyl metal hydride mechanism is proposed on the basis of various independent experiments in both homogeneous and biphasic systems [ sulphos = -O3S(C6H4)CH2C(CH2PPh2)(3)].
引用
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页码:11 / 12
页数:2
相关论文
共 14 条
[1]   RHODIUM(I)-CATALYZED BIPHASIC ISOMERIZATION OF ALLYLIC ALCOHOLS [J].
ALPER, H ;
HACHEM, K .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (11) :2269-2270
[2]   Aldehyde decarbonylation catalysis under mild conditions [J].
Beck, CM ;
Rathmill, SE ;
Park, YJ ;
Chen, JY ;
Crabtree, RH ;
Liable-Sands, LM ;
Rheingold, AL .
ORGANOMETALLICS, 1999, 18 (25) :5311-5317
[3]   HOMOGENEOUS CATALYSIS - CATALYTIC PRODUCTION OF SIMPLE ENOLS [J].
BERGENS, SH ;
BOSNICH, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :958-967
[4]   CHEMOSELECTIVE HYDROGEN-TRANSFER REDUCTION OF ALPHA,BETA-UNSATURATED KETONES CATALYZED BY ISOSTRUCTURAL IRON(II), RUTHENIUM(II), AND OSMIUM(II) CIS HYDRIDE ETA(2)-DIHYDROGEN COMPLEXES [J].
BIANCHINI, C ;
FARNETTI, E ;
GRAZIANI, M ;
PERUZZINI, M ;
POLO, A .
ORGANOMETALLICS, 1993, 12 (09) :3753-3761
[5]   ZWITTERIONIC METAL-COMPLEXES OF THE NEW TRIPHOSPHINE NAO3S(C6H4)CH2C(CH(2)PPH(2))(3) IN LIQUID BIPHASIC CATALYSIS - AN ALTERNATIVE TO TEFLON PONYTAILS FOR FACILE CATALYST SEPARATION WITHOUT WATER [J].
BIANCHINI, C ;
FREDIANI, P ;
SERNAU, V .
ORGANOMETALLICS, 1995, 14 (12) :5458-5459
[6]   Liquid-biphase hydrogenolysis of benzo[b]thiophene by rhodium catalysis [J].
Bianchini, C ;
Meli, A ;
Patinec, V ;
Sernau, V ;
Vizza, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) :4945-4954
[7]  
BOTTEGHI C, 1976, GAZZ CHIM ITAL, V106, P1131
[8]  
Bricout H, 1998, EUR J INORG CHEM, P1739
[9]  
COLLMAN JP, 1980, PRINCIPLES APPL ORGA, P496
[10]   Studies of high surface area Pt/MoO3 and Pt/WO3 catalysts for selective hydrogenation reactions.: II.: Reactions of acrolein and allyl alcohol [J].
Hoang-Van, C ;
Zegaoui, O .
APPLIED CATALYSIS A-GENERAL, 1997, 164 (1-2) :91-103