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.
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收藏
页码：493 / 495
页数：3
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