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学科主题: 金属有机化学
题名: Investigation of bis(tributyltin)-Initiated free radical cyclization reactions of 4-pentenyl iodoacetates
其他题名: 六丁基二锡引发碘乙酸4-戊烯酯的自由基环合反应研究
作者: Wang JH(王军华) ; Li CZ(李超忠)
通讯作者: 李超忠
刊名: J. Org. Chem.
发表日期: 2002-01-01
卷: 67, 期:4, 页:1271-1276
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所
英文摘要: Bis(tributyltin)-initiated atomtransfercyclization reactions of 4-pentenyl iodoacetates(1) at 80℃ led to the formations of 5-(3-iodopropyl)-substituted dihydro-2(3H)-furanones(3) in high yield. With BF^3.Et^2O as the catlyst, the reactions were run at room temperature to afford the corresponding γ-iodoheptanolactones(2), which could be further transformed into 3-(tetrahydro-2-furyl)propanoic acids(6) upon treatment with aqueous NaHCO^3. The reaction mechanism was postulated to be the 8-endo free radical cyclization to generate γ-iodoheptanolactones which easily underwent intramolecular nucleophilic substitution to form bicyclic acylium species (7) as the key intermediate. Subsequent attack by iodide ion furnished γ-lactones while attack by hydroxide ion gave the tetrahydrofuran derivatives.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000173901700031
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/22784
Appears in Collections:中科院天然产物有机化学重点实验室_期刊论文

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Recommended Citation:
Wang JH,Li CZ. Investigation of bis(tributyltin)-Initiated free radical cyclization reactions of 4-pentenyl iodoacetates[J]. J. Org. Chem.,2002,67(4):1271-1276.
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