REGIOSPECIFIC NICKEL CYANIDE AND PHASE-TRANSFER CATALYZED SYNTHESIS OF BETA,GAMMA-UNSATURATED ACIDS FROM ALLENES

被引：21

作者：

SATYANARAYANA, N

ALPER, H

AMER, I

机构：

[1] UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 6N5,ONTARIO,CANADA

[2] BEN GURION UNIV NEGEV,DEPT CHEM,IL-84105 BEER SHEVA,ISRAEL

来源：

ORGANOMETALLICS | 1990年 / 9卷 / 01期

关键词：

12;

D O I：

10.1021/om00115a045

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Allenes react with carbon monoxide in an aqueous base-toluene two-phase system, with cetyltrimethylammonium bromide as the phase-transfer agent and nickel cyanide as the metal catalyst, to give β,γ-unsaturated acids in 48-66% yields. This reaction proceeds under exceptionally mild conditions (90 °C, 1 atm), with the regiochemistry being opposite to that previously observed in hydrocarboxylation reactions. © 1990, American Chemical Society. All rights reserved.

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页码：284 / 286

页数：3

相关论文

共 12 条

[1] THE ALKOXY-ALKOXYCARBONYLATION OF ALLENES [J].

ALPER, H ;

HARTSTOCK, FW ;

DESPEYROUX, B .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (14) :905-906

[2]

ALPER H, 1987, ACS SYM SER, V326, P8

[3] LANTHANIDE-PROMOTED AND NICKEL CYANIDE CATALYZED CARBONYLATION REACTIONS UNDER PHASE-TRANSFER CONDITIONS [J].

AMER, I ;

ALPER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :927-930

[4] NICKEL CYANIDE AND PHASE-TRANSFER-CATALYZED CARBONYLATION OF ARYL IODIDES IN THE ABSENCE OF LIGHT [J].

AMER, I ;

ALPER, H .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5147-5148

[5] IODOLACTONIZATIONS USING THALLIUM(I) CARBOXYLATES [J].

CAMBIE, RC ;

HAYWARD, RC ;

ROBERTS, JL ;

RUTLEDGE, PS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (15) :1864-1867

[6]

DESABBAYES H, 1987, NEW J CHEM, V11, P535

[7]

GELIN R, 1976, CR ACAD SCI C CHIM, V283, P755

[8]

Jacobs T. L., 1982, CHEM ALLENES, V2, P277

[9] CYANONICKEL(II) COMPLEXES AS CATALYSTS FOR THE PHASE-TRANSFER-CATALYZED CARBONYLATION OF ALLYL HALIDES - THE ISOLATION OF THE CATALYTICALLY ACTIVE SPECIES [NI(CO)3CN-] [J].

JOO, F ;

ALPER, H .

ORGANOMETALLICS, 1985, 4 (10) :1775-1778

[10] SYNTHESIS AND MASS-SPECTRA OF SOME ALPHA,BETA-UNSATURATED GAMMA-LACTONES AND GAMMA-LACTAMS [J].

KING, GS ;

WAIGHT, ES .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (12) :1499-1504