Oxatriquinane and oxatriquinacene: Extraordinary oxonium ions

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

Research output: Contribution to journalArticle

33 Citations (Scopus)

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

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Ions
Chromatography
Sulfhydryl Compounds
Amines
Alcohols
Salts
Crystal structure
X-Rays
X rays
hydronium ion
1,4,7 cyclononatriene

ASJC Scopus subject areas

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

Cite this

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

Oxatriquinane and oxatriquinacene : Extraordinary oxonium ions. / Mascal, Mark; Hafezi, Nema; Meher, Nabin K.; Fettinger, James C.

In: Journal of the American Chemical Society, Vol. 130, No. 41, 15.10.2008, p. 13532-13533.

Research output: Contribution to journalArticle

Mascal, M, Hafezi, N, Meher, NK & Fettinger, JC 2008, 'Oxatriquinane and oxatriquinacene: Extraordinary oxonium ions', Journal of the American Chemical Society, vol. 130, no. 41, pp. 13532-13533. https://doi.org/10.1021/ja805686u
Mascal, Mark ; Hafezi, Nema ; Meher, Nabin K. ; Fettinger, James C. / Oxatriquinane and oxatriquinacene : Extraordinary oxonium ions. In: Journal of the American Chemical Society. 2008 ; Vol. 130, No. 41. pp. 13532-13533.
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