Face Selectivity in the 1,3-Dipolar Cycloaddition Reactions of Benzonitrile Oxide with 5-Substituted Adamantane-2-thiones and 2-Methyleneadamantanes

Wen-Sheng Chung*, Tzong Liang Tsai, Chia Chin Ho, M. Y.N. Chiang, W. J. Le Noble

*Corresponding author for this work

Research output: Contribution to journalArticle

26 Scopus citations

Abstract

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 Δ2-1,4,2-oxathiazolines (5-Xs) and two Δ2-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 product 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.

Original languageEnglish
Pages (from-to)4672-4676
Number of pages5
JournalJournal of Organic Chemistry
Volume62
Issue number14
DOIs
StatePublished - 1 Dec 1997

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