Oxatriquinane and oxatriquinacene: Extraordinary oxonium ions

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

doi:10.1021/ja805686u

Oxatriquinane and oxatriquinacene: Extraordinary oxonium ions

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

Chemistry

Research output: Contribution to journal › Article

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 language	English (US)
Pages (from-to)	13532-13533
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	41
DOIs	https://doi.org/10.1021/ja805686u
State	Published - 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

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