Generation of Cycloalkynes by Hydro-Iodonio-Elimination of Vinyl Iodonium Salts

详细信息    查看全文

• 作者：Tadashi Okuyama and Morifumi Fujita
• 刊名：Accounts of Chemical Research
• 出版年：2005
• 出版时间：August 2005
• 年：2005
• 卷：38
• 期：8
• 页码：679 - 686
• 全文大小：224K
• 年卷期：v.38,no.8(August 2005)
• ISSN：1520-4898

文摘

Cyclohexynes can be generated efficiently from 1-cyclohexenyliodonium salts with acetate or other bases via the E2 and E1mechanism. The observed regioselectivity of nucleophilic additionto substituted cyclohexynes conforms to the LUMO populations:the less deformed acetylenic carbon is more electrophilic. Cycloheptyne can form by the E1-type elimination via 1,2-rearrangementfrom cyclohexylidenemethyliodonium salt under very weakly basicconditions.