title: Functionalized oxatriquinanes and their structural equilibrium in protic solvent.
abstract: We synthesized oxatriquinane hexafluorophosphate bearing an ethoxycarbonylmethyl group 7 or a 2-oxopropyl group 11. Both of these organic oxonium cation compounds were obtained as stable solids. However, (1)H-NMR analysis showed that oxatriquinane 7 was present as the oxonium cation in aprotic solvent CD₃CN, but was in rapid equilibrium with ring-opened bicyclic compound 8 in protic solvent CD₃OD. The oxatriquinane 11 also showed similar behavior in protic solvent. Phenyl-substituted oxatriquinanes 12 and 14 were also obtained as stable solids, and showed similar properties to 7 and 11.
authors.affiliation: Research Foundation Itsuu Laboratory.
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Suzuki
authors.forename: Hideaki
authors.initials: H
authors.lastname: Muratake
mesh_terms: D015394:Molecular Structure; D066244:Proton Magnetic Resonance Spectroscopy; D011522:Protons; D011809:Quinones / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D011522:Protons; D011809:Quinones; D012997:Solvents