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J Am Chem Soc. 2008 Oct 15;130(41):13532-3. doi: 10.1021/ja805686u. Epub 2008 Sep 18.

Oxatriquinane and oxatriquinacene: extraordinary oxonium ions.

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  • 1Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, California 95616, USA.


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.

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