THE INSITU-GENERATED NICKEL(0)-CATALYZED HOMO-COUPLING OF ALKENYL HALIDES WITH ZINC POWDER - A SPECIFIC OUTCOME IN STEREOCHEMISTRY

被引：33

作者：

TAKAGI, K ^{[1
]}

MIMURA, H ^{[1
]}

INOKAWA, S ^{[1
]}

机构：

[1] OKAYAMA UNIV,FAC SCI,DEPT CHEM,OKAYAMA 700,JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1984年 / 57卷 / 12期

关键词：

CATALYSTS - CHEMICAL REACTIONS - Reaction Kinetics - POWDERS;

D O I：

10.1246/bcsj.57.3517

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The catalytic activity of nickel(0) generated in situ from nickel(II) salt was examined in a dehalogenative coupling of alkenyl halides with zinc powder. The reaction of alkenyl bromides took place provided that potassium iodide was present to assist the reduction of nickel(II) with zinc powder, and also to convert the alkenyl bromides to the corresponding alkenyl iodides. A speculative view concerning the disproportionation step is advanced in an attempt to explain the unique sterochemistry observed.

引用

页码：3517 / 3522

页数：6

共 46 条

[1] ALLENES .3. SYNTHESIS OF CYCLIC ALLENES
BALL, WJ
LANDOR, SR
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1962, (JUN): : 2298 - &
[2] BASOLO F, 1967, MECHANISMS INORGANIC, P495
[3] COMPLEX REDUCING AGENTS (CRAS) - VERSATILE, NOVEL WAYS OF USING SODIUM HYDRIDE IN ORGANIC-SYNTHESIS
CAUBERE, P
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (08): : 599 - 613
[4] NICKEL-CATALYSED REACTIONS OF ALLYL HALIDES AND RELATED COMPOUNDS
CHIUSOLI, GP
CASSAR, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (02) : 124 - +
[5] REACTIONS OF PALLADIUM(II) WITH ORGANIC COMPOUNDS .3. REACTIONS OF AROMATIC IODIDES IN BASIC-MEDIA
CLARK, FRS
NORMAN, ROC
THOMAS, CB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (02): : 121 - 125
[6] MECHANISMS OF ELIMINATION REACTIONS .2. THE SPONTANEOUS DECOMPOSITION OF SALTS OF BETA-HALO ACIDS .2. TRANS-CINNAMIC ACID DIBROMIDE
CRISTOL, SJ
NORRIS, WP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (11) : 2645 - 2646
[7] ORGANOPHOSPHINEPALLADIUM COMPLEXES AS CATALYSTS FOR VINYLIC HYDROGEN SUBSTITUTION-REACTIONS
DIECK, HA
HECK, RF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) : 1133 - 1136
[8] BETA-STYRYLCOBALOXIMES - MECHANISM OF FORMATION FROM BETA-STYRYL HALIDES AND MECHANISM OF CLEAVAGE BY ELECTROPHILES
DODD, D
JOHNSON, MD
MEEKS, BS
TITCHMARSH, DM
NGUYENVANDUONG, K
GAUDEMER, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (11): : 1261 - 1267
[9] DOLBY LJ, 1966, J ORG CHEM, V31, P1114
[10] THE 3RD ISOMERIC (CIS-TRANS-) MUCONIC ACID
ELVIDGE, JA
LINSTEAD, RP
SIMS, P
ORKIN, BA
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1950, (AUG): : 2235 - 2241

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