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-Jul-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
Appears in Collections:Conferences Paper


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