Diels-Alder approach to biaryls: Elucidation of competing tandem [2+2] cycloaddition/[1,3] sigmatropic shift pathway

被引：26

作者：

Ashburn, Bradley O. ^{[1
]}

Carter, Rich G. ^{[1
]}

Zakharov, Lev N. ^{[1
]}

机构：

[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 18期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/jo801245a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 2-halo-6-nitrophenylacetylene with an electron deficient diene gives rise to a [4+2] cycloaddition/cycloreversion biaryl product and a bicyclo[4.2.0]octadiene resulting from a competing [2+2] cycloaddition pathway. The cyclobutene can be opened to give a mixture of cyclooctatriene and biaryl in varying amounts depending on heat and light exposure. The conversion of the cyclobutene into biaryl occurs through a [1.3] signiatropic carbon shift followed by [4+2] cycloextrusion of ethylene gas.

引用

页码：7305 / 7309

页数：5

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