Study on the reactivity of oxabicyclic Alkenes in ruthenium-catalyzed [2+2] cycloadditions

被引：47

作者：

Burton, Ryan R. ^{[1
]}

Tam, William ^{[1
]}

机构：

[1] Univ Guelph, Dept Chem, Guelph Waterloo Ctr Grad Work Chem & Biochem, Guelph, ON N1G 2W1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 19期

关键词：

D O I：

10.1021/jo701383d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The ruthenium-catalyzed [2+2] cycloadditions of various bicyclic alkenes with an alkyne have been investigated. The presence of the oxygen in the bridgehead of the bicyclic alkene significantly enhanced the rate of the ruthenium-catalyzed [2+2] cycloadditions. The presence of a Cl-substutuent on the oxanorbornadiene, decreased the rate of the cycloaddition and electron-withdrawing Cl-substutuents were found to be more reactive than electron-donating Cl-substutuents in the Ru-catalyzed [2+2] cycloaddition. The nature of the substituent on the benzene ring of oxabenzonorbornadienes showed little effect on the rate of the cycloaddition.

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页码：7333 / 7336

页数：4

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