title: O-attack versus N-attack: electrophilic halocyclization of unsaturated amides with vinylic halogen substitution.
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.
authors.affiliation: 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.
authors.forename: Tianshun
authors.initials: T
authors.lastname: Hu
authors.forename: Kun
authors.initials: K
authors.lastname: Liu
authors.forename: Meihua
authors.initials: M
authors.lastname: Shen
authors.forename: Xinting
authors.initials: X
authors.lastname: Yuan
authors.forename: Yu
authors.initials: Y
authors.lastname: Tang
authors.forename: Chaozhong
authors.initials: C
authors.lastname: Li
mesh_terms: D000577:Amides / Q000737:chemistry*; D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000577:Amides; D006846:Hydrocarbons, Halogenated; D007659:Ketones