title: Oxatriquinane and oxatriquinacene: extraordinary oxonium ions.
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.
authors.affiliation: Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, California 95616, USA. mascal@chem.ucdavis.edu
authors.forename: Mark
authors.initials: M
authors.lastname: Mascal
authors.forename: Nema
authors.initials: N
authors.lastname: Hafezi
authors.forename: Nabin K
authors.initials: NK
authors.lastname: Meher
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger