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 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.
Mascal
Mark
M
Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, California 95616, USA. mascal@chem.ucdavis.edu
Hafezi
Nema
N
Meher
Nabin K
NK
Fettinger
James C
JC