SIMPLE STEREOSPECIFIC SYNTHESES OF (E)-1-CHLORO(OR BROMO)ALK-1-ENES FROM ALK-1-YNES VIA HYDROBORATION

被引:16
作者
MASUDA, Y
HOSHI, M
ARASE, A
机构
[1] Department of Industrial Chemistry, Kitami Institute of Technology
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 21期
关键词
D O I
10.1039/p19920002725
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereochemically pure (E)-1-chloro(or bromo)alk-1-enes were obtained in sufficiently good yields from alk-1 -ynes via hydroboration with dialkylborane followed by reactions with facile reagents; corresponding copper(II) halides, in the presence of a small amount of water, in polar aprotic solvents.
引用
收藏
页码:2725 / 2726
页数:2
相关论文
共 14 条
[1]   REACTIONS OF ORGANOBORANES WITH FERRIC-CHLORIDE AND THIOCYANATE - CONVENIENT SYNTHESES OF ALKYL CHLORIDES AND THIOCYANATES FROM OLEFINS VIA HYDROBORATION [J].
ARASE, A ;
MASUDA, Y ;
SUZUKI, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1974, 47 (10) :2511-2514
[2]   VINYLIC ORGANOBORANES .15. MERCURATION OF 2-ALKENYL-1,3,2-BENZODIOXABOROLES AND BORONIC ACIDS - A CONVENIENT STEREOSPECIFIC PROCEDURE FOR THE CONVERSION OF ALKYNES INTO (E)-1-HALO-1-ALKENES VIA MERCURIC-SALTS [J].
BROWN, HC ;
LAROCK, RC ;
GUPTA, SK ;
RAJAGOPALAN, S ;
BHAT, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6079-6084
[3]   VINYLIC ORGANOBORANES .13. A CONVENIENT STEREOSPECIFIC SYNTHESIS OF (Z)-1-HALO-1-ALKENES FROM 1-ALKYNES VIA (E)-1-ALKENYLBORANE DERIVATIVES WITH HALOGENS [J].
BROWN, HC ;
SUBRAHMANYAM, C ;
HAMAOKA, T ;
RAVINDRAN, N ;
BOWMAN, DH ;
MISUMI, S ;
UNNI, MK ;
SOMAYAJI, V ;
BHAT, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6068-6075
[4]   VINYLIC ORGANOBORANES .14. A STEREOSPECIFIC SYNTHESIS OF (E)-1-HALO-1-ALKENES FROM 1-ALKYNES [J].
BROWN, HC ;
HAMAOKA, T ;
RAVINDRAN, N ;
SUBRAHMANYAM, C ;
SOMAYAJI, V ;
BHAT, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6075-6079
[5]   VINYLIC ORGANOBORANES .12. SYNTHESIS OF (Z)-1-HALO-1-ALKENES VIA HYDROBORATION OF 1-HALO-1-ALKYNES FOLLOWED BY PROTONOLYSIS [J].
BROWN, HC ;
BLUE, CD ;
NELSON, DJ ;
BHAT, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6064-6067
[6]  
BROWN HC, 1975, ORGANIC SYNTHESIS VI, P54
[7]  
KABALKA GW, 1989, TETRAHEDRON LETT, P1483
[8]  
KUNDA SA, 1985, TETRAHEDRON LETT, P279
[10]   SELECTIVE ELIMINATION OF SECONDARY ALKYL GROUP FROM TRIALKYLBORANE BY THE SUCCESSIVE TREATMENTS WITH ANISOLE AND DIMETHYL-SULFOXIDE - SUPPLY OF THE SYNTHETIC INTERMEDIATE FOR PRIMARY ALKYL DERIVATIVES [J].
MASUDA, Y ;
HOSHI, M ;
ARASE, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (01) :271-272