STEREOCONTROLLED CARBOTITANATION OF ALKYNYLSILANES

被引：33

作者：

SNIDER, BB

KARRAS, M

机构：

[1] Department of Chemistry, Princeton University, Princeton

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1979年 / 179卷 / 03期

关键词：

D O I：

10.1016/S0022-328X(00)91752-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Carbometalation of alkynylsilanes with 1 1 titanocene dichloride/dialkylaluminum chloride is stereospecifically cis. The alkenyltitanium intermediate can be stereospecifically protonated by aqueous sodium hydroxide or iodinated. Addition of any Lewis base to the alkenyltitanium intermediate induces decomposition of this intermediate to give an alkene by hydrogen atom abstraction from the medium, with loss of stereochemistry. © 1979.

引用

收藏

页码：C37 / C41

页数：5

相关论文

共 16 条

[1]

CHAN TH, 1977, TETRAHEDRON LETT, P3317

[2] ALKENE SYNTHESIS VIA BETA-FUNCTIONALIZED ORGANOSILICON COMPOUNDS [J].

CHAN, TH .

ACCOUNTS OF CHEMICAL RESEARCH, 1977, 10 (12) :442-448

[3] ATTACK BY PHOSPHORUS NUCLEOPHILES ON A CLUSTER-BOUND VINYL GROUP - CRYSTAL-STRUCTURE OF HOS-3(CO)10(CHCH-2PME-2PH) [J].

CHURCHILL, MR ;

DEBOER, BG ;

SHAPLEY, JR ;

KEISTER, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (08) :2357-2358

[4] SILICON IN ORGANIC-SYNTHESIS [J].

COLVIN, EW .

CHEMICAL SOCIETY REVIEWS, 1978, 7 (01) :15-64

[5] ORGANOMETALLIC COMPOUNDS OF GROUP 3 .36. REGIOSPECIFIC AND STEREOSELECTIVE CARBOMETALLATION OF ALKYNYLSILANES BY ZIEGLER-NATTA ALKYLATING-AGENTS [J].

EISCH, JJ ;

MANFRE, RJ ;

KOMAR, DA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 159 (04) :C13-C19

[6]

HUGGINS JM, 1979, J AM CHEM SOC, V101, P4410, DOI 10.1021/ja00509a078

[7] CONJUGATE ADDITION OF VINYL-COPPER COMPLEXES DERIVED FROM ADDITION OF ALKYL-COPPER COMPLEXES TO ACETYLENES - STEREOSPECIFIC SYNTHESIS OF TRISUBSTITUTED OLEFINS [J].

MARFAT, A ;

MCGUIRK, PR ;

KRAMER, R ;

HELQUIST, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (01) :253-255

[8] HIGHLY STEREOSELECTIVE SYNTHESIS OF VINYL BROMIDES AND CHLORIDES VIA DISUBSTITUTED VINYLSILANES [J].

MILLER, RB ;

MCGARVEY, G .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (23) :4424-4431

[9]

NORMANT JF, 1976, J ORGANOMET CHEM LIB, V1, P219

[10] BROMINE-LITHIUM EXCHANGE IN VINYL AND ARYL BROMIDES WITH TERT-BUTYL LITHIUM - RING ENLARGEMENT VIA DIBROMOCARBENE ADDUCTS [J].

SEEBACH, D ;

NEUMANN, H .

CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (03) :847-853