Oxatriquinane and oxatriquinacene: Extraordinary oxonium ions

Mark Mascal, Nema Hafezi, Nabin K. Meher, James C. Fettinger

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

Oxatriquinane, a fused, tricyclic alkyl oxonium ion of unprecented stability, was synthesized in five steps from 1,4,7-cyclononatriene. It survives reflux in H2O, chromatography, and attack by alcohols, alkyl thiols, halide ions, and hindered amine bases. The X-ray crystal structure shows longer C-O bond distances and more acute C-O-C bond angles than any reported alkyloxonium salt. The corresponding oxatriquinene and oxatriquinacene were also synthesized and represent the first examples of stable allyl oxonium species.

Original languageEnglish (US)
Pages (from-to)13532-13533
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number41
DOIs
StatePublished - Oct 15 2008

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

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    Mascal, M., Hafezi, N., Meher, N. K., & Fettinger, J. C. (2008). Oxatriquinane and oxatriquinacene: Extraordinary oxonium ions. Journal of the American Chemical Society, 130(41), 13532-13533. https://doi.org/10.1021/ja805686u