NICKEL-CATALYZED CARBONYLATION OF ALPHA-KETO ALKYNES UNDER PHASE-TRANSFER CONDITIONS

被引：29

作者：

ARZOUMANIAN, H ^{[1
]}

JEAN, M ^{[1
]}

NUEL, D ^{[1
]}

CABRERA, A ^{[1
]}

GUTIERREZ, JLG ^{[1
]}

ROSAS, N ^{[1
]}

机构：

[1] NATL AUTONOMOUS UNIV MEXICO,INST QUIM,MEXICO CITY 04510,DF,MEXICO

来源：

ORGANOMETALLICS | 1995年 / 14卷 / 11期

关键词：

D O I：

10.1021/om00011a071

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

alpha-Keto alkynes are carbonylated in the presence of Ni(CN)(2) under phase transfer conditions (toluene, 5 N NaOH, tetrabutylammonium bromide) to give either unsaturated hydroxybutyrolactones or 2-alkynylidene 3-keto carboxylic acids depending on. the presence or absence of an alpha-H on the carbon alpha to the alkynyl group. This is rationalized, in the second case, by a rearrangement following abstraction of this alpha-H by base. A rearrangement to an allenic intermediate prior to carbonylation is excluded.

引用

页码：5438 / 5441

页数：4

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