Details

Autor(en) / Beteiligte

• Hu, Tianshun
• Liu, Kun
• Shen, Meihua
• Yuan, Xinting
• Tang, Yu
• Li, Chaozhong

Titel

O-Attack versus N-Attack:  Electrophilic Halocyclization of Unsaturated Amides with Vinylic Halogen Substitution

Ist Teil von

• Journal of organic chemistry, 2007-10, Vol.72 (22), p.8555-8558

Ort / Verlag

Washington, DC: American Chemical Society

Erscheinungsjahr

2007

Quelle

MEDLINE

Beschreibungen/Notizen

• 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.