O-attack versus N-attack: Electrophilic halocyclization of unsaturated amides with vinylic halogen substitution

被引：36

作者：

Hu, Tianshun ^{[1
]}

Liu, Kun ^{[1
]}

Shen, Meihua ^{[1
]}

Yuan, Xinting ^{[1
]}

Tang, Yu ^{[1
]}

Li, Chaozhong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Joint Lab Green Synthet Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 22期

关键词：

D O I：

10.1021/jo7016444

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic iodocyclization of unsaturated amides with an internal vinylic halogen (Cl, Br, or I) substitution afforded exclusively the corresponding cyclic iminoketones via iodolactamization. On the other hand, amides having a terminal vinylic halogen substituent underwent iodolactonization only. Theoretical calculations revealed that the iodocyclization proceeds via the intramolecular iodonium ion transfer from the amide nitrogen to the C=C double bond.

引用

页码：8555 / 8558

页数：4

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