Oxatriquinane and Oxatriquinacene: Extraordinary Oxonium Ions

Oxatriquinane and Oxatriquinacene: Extraordinary Oxonium Ions

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...

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Veröffentlicht in:Journal of the American Chemical Society 2008-10, Vol.130 (41), p.13532-13533
Hauptverfasser: Mascal, Mark, Hafezi, Nema, Meher, Nabin K, Fettinger, James C
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creator Mascal, Mark
Hafezi, Nema
Meher, Nabin K
Fettinger, James C
description 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.
doi_str_mv 10.1021/ja805686u
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title Oxatriquinane and Oxatriquinacene: Extraordinary Oxonium Ions
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