標題: | Face selectivity in the 1,3-dipolar cycloaddition reactions of benzonitrile oxide with 5-substituted adamantane-2-thiones and 2-methyleneadamantanes |
作者: | Chung, WS Tsai, TL Ho, CC Chiang, MYN leNoble, WJ 應用化學系 Department of Applied Chemistry |
公開日期: | 11-七月-1997 |
摘要: | The 1,3-dipolar cycloaddition reactions of benzonitrile oxide with 5-substituted adamantane-2-thiones (2-X) and 2-methyleneadamantanes (3-X) produced two geometrically isomeric Delta(2)-1,4,2-oxathiazolines (5-Xs) and two Delta(2)-isoxazolines (6-Xs), respectively. The substituent was varied from fluoro, chloro, bromo, to phenyl. X-ray single-crystal analysis confirmed the configuration of (Z)-5-F. The produce formation bias resulting from the favored attack of nitrile oxide on the zu-face is discussed in terms of transition-state hyperconjugation and frontier molecular orbital theory. |
URI: | http://hdl.handle.net/11536/439 |
ISSN: | 0022-3263 |
期刊: | JOURNAL OF ORGANIC CHEMISTRY |
Volume: | 62 |
Issue: | 14 |
起始頁: | 4672 |
結束頁: | 4676 |
顯示於類別: | 會議論文 |