REACTIONS OF 1,1-DIHALOALKENES WITH TRIORGANOZINCATES - A NOVEL METHOD FOR THE PREPARATION OF ALKENYLZINC SPECIES ASSOCIATED WITH CARBON-CARBON BOND FORMATION

被引：95

作者：

HARADA, T

KATSUHIRA, T

HARA, D

KOTANI, Y

MAEJIMA, K

KAJI, R

OKU, A

机构：

[1] Department of Chemistry, Kyoto Institute of Technology, Kyoto 606, Matsugasaki, Sakyo-ku

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 18期

关键词：

D O I：

10.1021/jo00070a027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithium trialkylzincates react with 1,1-dibromoalkenes 1 and 1-bromo-1-chloroalkenes 2 at -85-degrees-C in THF to give 1-bromoalkenes 5 and 1-chloroalkenes 7, respectively, upon hydrolysis. The intermediate (1-haloalkenyl)zincates 4 and 6 are stable at low temperature but, when allowed to warm to 0-degrees-C, they undergo a 1,2-alkyl migration reaction to afford alkenylzinc species 10. A variety of alkylation products 11 are obtained by the hydrolysis of 10. In the presence of (Ph3P)2Pd (5 mol%), alkenylzinc species 10 react smoothly with organic halides (AcCl, EtOCOCl, CH2=CH-(Me)Br, PhBr) to yield the corresponding coupling products 13-16.

引用

页码：4897 / 4907

页数：11

共 69 条

[61] THE OLEFINATION OF FUNCTIONALIZED ALKYLIDENEMALONATES BY 1,1-DIMETALLOALKANES - A NEW CHEMOSELECTIVE AND STEREOSELECTIVE PREPARATION OF FUNCTIONALIZED OLEFINS [J].