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贫电子环丙烷衍生物与胂叶立德的反应研究
引用本文:陈雅丽,曹卫国,丁维钰,孙晓华.贫电子环丙烷衍生物与胂叶立德的反应研究[J].中国化学,2005,23(1):81-84.
作者姓名:陈雅丽  曹卫国  丁维钰  孙晓华
作者单位:[1]DepartmentofChemistry,ShanghaiUniversity,Shanghai200436,China [2]DepartmentofChemistry,ShanghaiUniversity,Shanghai200436,China//StateKeyLaboratoryofOrganometallicChemistry,ChineseAcademyofSciences,Shanghai200032,China
摘    要:The reaction of electron-deficient cyclopropane derivatives, cis-1-methoxycarbonyl-2-aryl-6,6-dimethyl-5,7dioxospiro2,5]octa-4,8-diones with benzoylmethylenetriphenylarsorane (2) and methoxycarbonylmethylenetriphenylarsorane (4) was found to form cis,trans-l-methoxycarbonyl-2-aryl-3-benzoyl-7,7-dimethyl-6,8-dioxospiro3,5]nona-5,9-dione (3a-3e) and trans,cis,trans-5-2‘-methoxycarbonyl-2‘-(triphenylarsoranylidene)acetyl]-6oxo-3-aryl-tetrahydro-pyran-2,4-dicarboxylic acid dimethyl esters (5a-5c) respectively with high stereoselectivity. The possible reaction mechanisms for the formation of the different products were also orooosed.

关 键 词:环丙烷衍生物  砷内翁盐  立体选择性  反应机理
收稿时间:2004-5-18
修稿时间:2004-9-13

Study on the Reaction of Electron‐deficient Cyclopropane Derivatives with Arsonium Ylides
Ya‐Li Chen,Wei‐Guo Cao,Wei‐Yu Ding,Xiao‐Huaa Sun.Study on the Reaction of Electron‐deficient Cyclopropane Derivatives with Arsonium Ylides[J].Chinese Journal of Chemistry,2005,23(1):81-84.
Authors:Ya‐Li Chen  Wei‐Guo Cao  Wei‐Yu Ding  Xiao‐Huaa Sun
Abstract:The reaction of electron‐deficient cyclopropane derivatives, cis‐1‐methoxycarbonyl‐2‐aryl‐6,6‐dimethyl‐5,7‐dioxospiro2,5]octa‐4,8‐diones with benzoylmethylenetriphenylarsorane ( 2 ) and methoxycarbonylmethylene‐triphenylarsorane ( 4 ) was found to form cis,trans‐1‐methoxycarbonyl‐2‐aryl‐3‐benzoyl‐7,7‐dimethyl‐6,8‐dioxo‐spiro3,5]nona‐5,9‐dione ( 3a – 3e ) and trans, cis,trans‐5‐2′‐methoxycarbonyl‐2′‐(triphenylarsoranylidene)acetyl]‐6‐oxo‐3‐aryl‐tetrahydro‐pyran‐2,4‐dicarboxylic acid dimethyl esters ( 5a – 5c ) respectively with high stereoselectivity. The possible reaction mechanisms for the formation of the different products were also proposed.
Keywords:cyclopropane derivative  arsonium ylide  weak nucleophile  stereoselectivity
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