MONOCARBOXYLATION AND DICARBOXYLATION OF ALPHA-HALOALKYNES CATALYZED BY NICKEL CYANIDE UNDER PHASE-TRANSFER CONDITIONS

被引：25

作者：

ARZOUMANIAN, H

COCHINI, F

NUEL, D

PETRIGNANI, JF

ROSAS, N

机构：

[1] Ecole Nationals Supérieure de Synthèses, Procedes et d'Ingénlérie Chimiques d'Aix-MarseiHe, URA du CRNS 1410, Université d'Aix-Marseille III

来源：

ORGANOMETALLICS | 1992年 / 11卷 / 01期

关键词：

D O I：

10.1021/om00037a086

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Alpha-Haloalkynes react with carbon monoxide to give either allenic monoacids or unsaturated diacids in 70-96% overall yields. The reaction is catalyzed by nickel cyanide under phase-transfer conditions (4-methyl-2-pentanone, 5 N NaOH, tetraalkylammonium halide). It is shown that the carbonylation occurs stepwise: first to the allenic monoacid via a nucleophilic substitution, followed by a second carbonylation of this latter. The diacid is obtained with high stereoselectivity.

引用

页码：493 / 495

页数：3

共 24 条

[1] MILD, REGIOSPECIFIC HYDROCARBOXYLATION OF ALKYNES CATALYZED BY NICKEL CYANIDE UNDER PHASE-TRANSFER CONDITIONS [J].

AMER, I ;

ALPER, H .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 383 (1-3) :573-577

[2]

ARZOUMANIAN H, UNPUB

[3]

CASSAR L, 1973, SYNTHESIS-STUTTGART, P509

[4]

CHUISOLI GP, 1959, CHIM IND-MILAN, V41, P513

[5]

CHUISOLI GP, 1959, CHIM IND-MILAN, V41, P506

[6]

JOLLY PW, 1982, COMPREHENSIVE ORGANO, V8, P773

[7] RESEARCHES ON ACETYLENIC COMPOUNDS .62. A GENERAL SYNTHESIS OF ALLENIC ACIDS [J].

JONES, ERH ;

WHITHAM, GH ;

WHITING, MC .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (NOV) :4628-4633

[8] RESEARCHES ON ACETYLENIC COMPOUNDS .22. THE REACTION BETWEEN NICKEL CARBONYL AND MONOSUBSTITUTED ACETYLENIC COMPOUNDS [J].

JONES, ERH ;

SHEN, TY ;

WHITING, MC .

JOURNAL OF THE CHEMICAL SOCIETY, 1950, (JAN) :230-236

[9] RESEARCHES ON ACETYLENIC COMPOUNDS .29. THE REACTION BETWEEN NICKEL CARBONYL AND DISUBSTITUTED ACETYLENES [J].

JONES, ERH ;

SHEN, TY ;

WHITING, MC .

JOURNAL OF THE CHEMICAL SOCIETY, 1951, (JAN) :48-52

[10] 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

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