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学科主题: 有机化学
题名: Control of the regioselectivity of sulfonamidyl radical cyclization by vinylic halogen substitution
其他题名: 通过烯基卤素取代控制磺酰胺氮自由基环合反应的区域选择性
作者: Lu HJ(陆红健) ; Chen Q(陈迁) ; Li CZ(李超忠)
通讯作者: 李超忠
刊名: J. Org. Chem.
发表日期: 2007
卷: 72, 期:7, 页:2564-2569
收录类别: SCI
部门归属: 上海有机所
英文摘要: The radical cyclization reactions of unsaturated sulfonamides were investigated. The photolysis of N-(4-halo-4-pentenyl) sulfonamides (X = I, Br, or Cl) with (diacetoxyiodo) benzene (DIB) and iodine at room temperature afforded exclusively the corresponding piperidines in 73-98% yield via 6-endo radical cyclization. On the other hand, the reactions of N-(5-halo-4-pentenyl) sulfonamides with DIB/I-2 led to the only formation of the pyrrolidine products in 84-99% yield via 5-exo radical cyclization. The vinylic halogen substitution not only successfully inhibits the competing ionic iodocyclization process to allow the radical cyclization to proceed smoothly but also shows a remarkable effect in controlling the regioselectivity of cyclization.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000245118900039
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/22832
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:
Lu HJ,Chen Q,Li CZ. Control of the regioselectivity of sulfonamidyl radical cyclization by vinylic halogen substitution[J]. J. Org. Chem.,2007,72(7):2564-2569.
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