O-attack versus N-attack: electrophilic halocyclization of unsaturated amides with vinylic halogen substitution |
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| Authors: | Hu Tianshun Liu Kun Shen Meihua Yuan Xinting Tang Yu Li Chaozhong |
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| Institution: | Joint Laboratory of Green Synthetic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, People's Republic of China. |
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| Abstract: | 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. |
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