Ruthenium catalysed oxidation without CCl4 of oleic acid, other monoenic fatty acids and alkenes

被引：79
作者：
Zimmermann, FO
Meux, E
Mieloszynski, JL
Lecuire, JM
Oget, N
机构：
[1] Univ Metz, EA 3471, Lab Chim & Applicat, F-57078 Metz, France
[2] Univ Metz, UMR 7555, Lab Electrochim Mat, F-57078 Metz, France
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 18期
关键词：
ruthenium; oxidatiow; oleic; fatty acids;
D O I：
10.1016/j.tetlet.2005.03.052
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ruthenium catalysed oxidation of alkenes and monoenic fatty acids is reported. The study of the influence of cosolvents (H2O/MeCN/X) shows that toxic CCl4 initially used in the Sharpless system (H2O/MeCN/CCl4) can be avoided and demonstrates that the oxidative cleavage of C=C bond could be accomplished in good yields with H2O/MeCN/AcOEt solvent system in a ratio 3/2/2, respectively. (c) 2005 Elsevier Ltd. All rights reserved.
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收藏
页码：3201 / 3203
页数：3
相关论文
共 26 条
[1]   Efficient oxidative cleavage of olefins to carboxylic acids with hydrogen peroxide catalyzed by methyltrioctylammonium tetrakis (oxodiperoxotungsto)phosphate (3-) under two-phase conditions.: Synthetic aspects and investigation of the reaction course [J].
Antonelli, E ;
D'Aloisio, R ;
Gambaro, M ;
Fiorani, T ;
Venturello, C .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7190-7206
[2]   NATURAL FATS AND OILS - RENEWABLE RAW-MATERIALS FOR THE CHEMICAL-INDUSTRY [J].
BAUMANN, H ;
BUHLER, M ;
FOCHEM, H ;
HIRSINGER, F ;
ZOEBELEIN, H ;
FALBE, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (01) :41-62
[3]   Cleavage of olefinic double bonds by mediated anodic oxidation [J].
Bäumer, US ;
Schäfer, HJ .
ELECTROCHIMICA ACTA, 2003, 48 (05) :489-495
[4]  
Biermann U, 2000, ANGEW CHEM INT EDIT, V39, P2206, DOI 10.1002/1521-3773(20000703)39:13<2206::AID-ANIE2206>3.0.CO
[5]  
2-P
[6]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[7]   THE OXIDATION OF OLEIC-ACID BY PERMANGANATE IN OIL IN WATER EMULSION [J].
GARTI, N ;
AVNI, E .
COLLOIDS AND SURFACES, 1982, 4 (01) :33-41
[8]  
Goebel C.G., US Patent, Patent No. [2813113, 2813113A]
[9]   Fats and oils as oleochemical raw materials [J].
Hill, K .
PURE AND APPLIED CHEMISTRY, 2000, 72 (07) :1255-1264
[10]   Electrochemical oxidation of iodate to periodate [J].
Janssen, LJJ ;
Blijlevens, MHA .
ELECTROCHIMICA ACTA, 2003, 48 (25-26) :3959-3964
123