NOVEL NI0-CATALYZED PREPARATION OF 3-CYCLOPENTENECARBOXYLIC ANILIDES FROM CYCLOPENTENES AND PHENYLISOCYANATE

被引:16
作者
HOBERG, H
NOHLEN, M
机构
[1] Max-Planck-Institut für Kohlenforschung, Postfach 101353, Kaiser-Wilhelm-Platz 1
关键词
D O I
10.1016/0022-328X(90)85236-R
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Cyclopentenes react with isocyanate on (Lig)Ni0-systems to form the bicyclic 5-azanickelacyclopentan-4-one derivates. The geometry of these butterfly complexes favors β-elimination of the β′-hydrogen atoms over that of the β- or β″-hydrogen. In a catalytic reaction the unsaturated amides 3-cyclopentene-carboxylic amide or 2-methylcyclopentene-3-carboxylic amide, both of which are substituted in position 3, are formed with high selectivity. © 1990.
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页码:C6 / C10
页数:5
相关论文
共 9 条
[1]   PI-ALLYLHYDRIDONICKEL COMPOUNDS [J].
BONNEMANN, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1970, 9 (09) :736-+
[2]  
BONNEMANN H, 1970, ANGEW CHEM, V82, P699
[3]   NICKEL(0)-CATALYZED PREPARATION OF ISOMERIC CARBOXAMIDES - LIGAND-CONTROLLED BETA-H OR BETA'-H ELIMINATION [J].
HOBERG, H ;
GUHL, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (08) :1035-1036
[4]   C-C BOND FORMING OF ALKENES WITH ISOCYANATES ON NICKEL(0) [J].
HOBERG, H ;
SUMMERMANN, K ;
MILCHEREIT, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 288 (02) :237-248
[5]  
Hoberg H., 1989, ANGEW CHEM, V101, P1091
[6]  
HOBERG H, 1988, J ORGANOMET CHEM, V358, P7
[7]   STERIC EFFECTS OF PHOSPHORUS LIGANDS IN ORGANOMETALLIC CHEMISTRY AND HOMOGENEOUS CATALYSIS [J].
TOLMAN, CA .
CHEMICAL REVIEWS, 1977, 77 (03) :313-348
[8]   FORMATION OF THE NICKELA-CYCLIC AMIDE COMPLEX 1-TRICYCLOHEXYLPHOSPHINO-4-METHYL-1,2-AZANICKELACYCLOPENTAN-3-ONE BY THE REACTION OF METHACRYLAMIDE WITH BIS(CYCLO-OCTADIENE)NICKEL IN THE PRESENCE OF TRICYCLOHEXYLPHOSPHINE [J].
YAMAMOTO, T ;
IGARASHI, K ;
ISHIZU, J ;
YAMAMOTO, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (13) :554-555
[9]   PREPARATION AND PROPERTIES OF PHOSPHINE COMPLEXES OF NICKEL-CONTAINING CYCLIC AMIDES AND ESTERS [(PR3) NICHZCH(RI)CONRZ][(PR3) NICHZCH(RI)COO] [J].
YAMAMOTO, T ;
IGARASHI, K ;
KOMIYA, S ;
YAMAMOTO, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (25) :7448-7456