THE RU(ETA(6)-NAPHTHALENE)(ETA(4)-CYCLOOCTA-1,5-DIENE)/ACETONITRILE SYSTEM IN THE SELECTIVE DIMERIZATION OF METHYL ACRYLATE TO TRANS-DIMETHYL-2-HEXENEDIOATE

被引:63
作者
PERTICI, P [1 ]
BALLANTINI, V [1 ]
SALVADORI, P [1 ]
BENNETT, MA [1 ]
机构
[1] AUSTRALIAN NATL UNIV,RES SCH CHEM,CANBERRA,ACT 0200,AUSTRALIA
关键词
D O I
10.1021/om00005a063
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The complex Ru(eta(6)-naphthalene)(eta(4)-cycloocta-1,5-diene), I, in the presence of acetonitrile, selectively catalyzes the tail-to-tail dimerization of methyl acrylate to trans-dimethyl-2-hexenedioate at 140 degrees C. An examination of the stoichiometric reaction between I and methyl acrylate shows that acetonitrile promotes removal of the dimer from the coordination sphere of ruthenium. Using tetrahydrofuran or N-methyl-2-pyrrolidinone as solvents, a long-lived catalyst is obtained which can be re-used without appreciable loss of activity.
引用
收藏
页码:2565 / 2569
页数:5
相关论文
共 24 条
[1]   OLEFIN-TO-OLEFIN ADDITION REACTIONS [J].
ALDERSON, T ;
JENNER, EL ;
LINDSEY, RV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (24) :5638-&
[2]  
ALDERSON T, 1961, Patent No. 3013066
[3]   PROTONATION OF DIENE COMPLEXES OF RHODIUM, IRIDIUM, RUTHENIUM, AND OSMIUM - A FINE BALANCE BETWEEN TERMINAL AND AGOSTIC HYDRIDES [J].
BENNETT, MA ;
MCMAHON, IJ ;
PELLING, S ;
BROOKHART, M ;
LINCOLN, DM .
ORGANOMETALLICS, 1992, 11 (01) :127-138
[4]   (ETA-6-NAPHTHALENE)(ETA-4-1,5-CYCLOOCTADIENE)RUTHENIUM(0) - EFFICIENT SYNTHESIS, CHEMISTRY, AND CATALYTIC PROPERTIES [J].
BENNETT, MA ;
NEUMANN, H ;
THOMAS, M ;
WANG, XQ ;
PERTICI, P ;
SALVADORI, P ;
VITULLI, G .
ORGANOMETALLICS, 1991, 10 (09) :3237-3245
[5]   CATALYTIC TAIL-TO-TAIL DIMERIZATION OF METHYL ACRYLATE USING RH(III) CATALYSTS [J].
BROOKHART, M ;
SABOETIENNE, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2777-2779
[6]   MECHANISM OF RHODIUM(III)-CATALYZED METHYL ACRYLATE DIMERIZATION [J].
BROOKHART, M ;
HAUPTMAN, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4437-4439
[7]  
GRENOUILLET P, 1987, Patent No. 2596390
[8]   PHOTOCHEMICAL-SYNTHESIS OF BIS(ETA-2-METHYL ACRYLATE)TRICARBONYLRUTHENIUM [J].
GREVELS, FW ;
REUVERS, JGA ;
TAKATS, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (05) :452-&
[9]  
GREVELS FW, 1974, ANGEW CHEM INT EDIT, V13, P534, DOI 10.1002/anie.197405341
[10]   STOICHIOMETRIC DIMERIZATION OF METHYL ACRYLATE MEDIATED BY PD(ACAC)2.HBF4 SYSTEMS AND ITS RELEVANCE TO THE MECHANISM OF CATALYTIC DIMERIZATION OF ACRYLATES (HACAC = MECOCH2COME) [J].
GUIBERT, I ;
NEIBECKER, D ;
TKATCHENKO, I .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1850-1852