Browsing by Author "Chiang, MYN"

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Face selectivity in the 1,3-dipolar cycloaddition reactions of benzonitrile oxide with 5-substituted adamantane-2-thiones and 2-methyleneadamantanes
(1997-07-11)
Chung, WS
;
Tsai, TL
;
Ho, CC
;
Chiang, MYN
;
leNoble, WJ
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.