Functionalized Oxatriquinanes and Their Structural Equilibrium in Protic Solvent

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, 1H-NMR analysis showed that oxatriquinane 7 was present as the oxonium cation in aprotic solvent...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2014/09/01, Vol.62(9), pp.921-926
Hauptverfasser:	Suzuki, Hideyuki, Muratake, Hideaki
Format:	Artikel
Sprache:	eng
Schlagworte:	equilibrium Molecular Structure organic oxonium cation oxatriquinane protic solvent Proton Magnetic Resonance Spectroscopy Protons Quinones - chemistry Solvents - chemistry Spectrometry, Mass, Electrospray Ionization
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Beschreibung
Zusammenfassung:	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, 1H-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.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.c14-00384