Regioselectivity in the Pauson-Khand reaction of allenic hydrocarbons

被引:26
|
作者
Antras, F [1 ]
Ahmar, M [1 ]
Cazes, B [1 ]
机构
[1] Univ Lyon 1, CNRS, Lab Chim Organ 1, F-69622 Villeurbanne, France
关键词
Pauson Khand reaction; allene; cycloaddition; cyclopentenone; cobalt complex;
D O I
10.1016/S0040-4039(01)01749-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselectivity of the cobalt-mediated cocyclisation of alkynes with allenic hydrocarbons leading to 4- and 5-alkylidenecyclopentenones was shown to depend on the substitution pattern of both the acetylenic and allenic components. An initial pseudoaxial coordination of the allenic hydrocarbon may account for the formation of the 5-alkylidenecyclopentenone from acetylene. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8153 / 8156
页数:4
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