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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Mascal et al. (2008) studied this question.
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