A Hydroxy‐Substituted Trialkyloxonium Ion and Its Oxonium Alkoxide Zwitterion
symmetric oxatriquinanetriol can be simply accessed by reaction of the tris-epoxide of 1,4,7-cyclononatriene with aqueous acid. The three OH groups of this hemispherical cation point into the endo space of the bowl and participate in strong intramolecular hydrogen bonding. A close balance in the dynamics of proton exchange between these hydroxy functions and amine bases is predicted by modeling. In practice, treatment of oxatriquinanetriol with the non-nucleophilic base 2-tert-butyl-1,1,3,3-tetramethylguanidine (Barton's base) leads to a zwitterionic oxonium alkoxide.
Authors
- Shuhei Manabe (ORCID: https://orcid.org/0000-0002-3299-4922)
- Görkem Günbaş (ORCID: https://orcid.org/0000-0003-2279-3032)
- Wondimagegn T. Shewa
- Mark Mascal (ORCID: https://orcid.org/0000-0001-7841-253X)
- Andrew L. Otsuki (ORCID: https://orcid.org/0000-0003-4483-2004)
- Gizem Atakan Alkan (ORCID: https://orcid.org/0000-0001-6824-259X)
- James C. Fettinger (ORCID: https://orcid.org/0000-0002-6428-4909)
- Nema Hafezi
Institutions
- Middle East Technical University (TR)
- University of California, Davis (US)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2026-05-11
- DOI
- https://doi.org/10.1002/anie.2727232
- Primary Topic
- Chemical Reactions and Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Science Foundation
- National Institutes of Health