PALLADIUM-CATALYZED REACTION OF (E)-DICHLOROETHENE AND (Z)-DICHLOROETHENE WITH 1-ALKYNES - AN EFFICIENT STEREOSPECIFIC SYNTHESIS OF (E)-ENEDIYNES AND (Z)-ENEDIYNES

被引:76
作者
CHEMIN, D
LINSTRUMELLE, G
机构
[1] Laboratoire de chimie, Ecole Normale Supérieure, 75231 Paris Cedex 05
关键词
D O I
10.1016/S0040-4020(01)80691-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereospecific sequential substitution of(E) and (Z)-dichloroethenes with 1-alkynes leads to (E) and (Z)-enediynes in high yield.
引用
收藏
页码:5335 / 5344
页数:10
相关论文
共 34 条
[1]   AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL CHLORIDES WITH TERMINAL ACETYLENES [J].
ALAMI, M ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1991, 32 (43) :6109-6112
[2]   RATES AND MECHANISM OF THE REVERSIBLE OXIDATIVE ADDITION OF (Z)-1,2-DICHLOROETHYLENE AND (E)-1,2-DICHLOROETHYLENE TO LOW-LIGATED ZERO-VALENT PALLADIUM [J].
AMATORE, C ;
AZZABI, M ;
JUTAND, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1670-1677
[3]   A CONVENIENT SYNTHESIS OF PROTECTED E-ENYNALS VIA CROSS COUPLING OF VINYLTIN ACETALS WITH BROMOALKYNES [J].
BEAUDET, I ;
PARRAIN, JL ;
QUINTARD, JP .
TETRAHEDRON LETTERS, 1992, 33 (25) :3647-3650
[4]  
Bohlmann F., 1973, NATURALLY OCCURRING
[5]   STEREOSPECIFIC SYNTHESES AND SPECTROSCOPIC PROPERTIES OF ISOMERIC 2,4,6,8-UNDECATETRAENES - NEW HYDROCARBONS FROM THE MARINE BROWN ALGA-GIFFORDIA-MITCHELLAE .4. [J].
BOLAND, W ;
SIELER, C ;
FEIGEL, M .
HELVETICA CHIMICA ACTA, 1987, 70 (04) :1025-1040
[6]   A NEW EFFICIENT SYNTHESIS OF (5S,12S)-DIHETE [J].
CHEMIN, D ;
ALAMI, M ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1992, 33 (19) :2681-2684
[7]   A SHORT STEREOCONTROLLED SYNTHESIS OF LEUKOTRIENE-B4 [J].
CHEMIN, D ;
LINSTRUMELLE, G .
TETRAHEDRON, 1992, 48 (10) :1943-1952
[8]   SUBSTITUTION OF 1-HALO-1-ALKYNES BY ORGANOMETALLIC DERIVATIVES OF COPPER - SYNTHESIS OF NEW CLASS OF SYNTHONS - APPLICATION TO SYNTHESIS OF BOMBYKOL [J].
COMMERCON, A ;
NORMANT, JF ;
VILLIERAS, J .
TETRAHEDRON, 1980, 36 (09) :1215-1221
[9]   (E)-3-(TRIMETHYLSILYL)-2-PROPEN-1-OL - AN IMPROVED PREPARATION [J].
DENMARK, SE ;
JONES, TK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (23) :4595-4597
[10]  
DOOLITTLE RE, 1984, SYNTHESIS-STUTTGART, P730