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Updated: Dec 7, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Novel keto-enol tautomerism in 1,3,5-trihydroxybenzene systems
Makabodee Ruaysap1, Stuart R Kennedy1, Collin M Mayhan1
1Department of Chemistry, University of Missouri, 601 S. College Avenue, Columbia, MO 65211, USA. AtwoodJ@missouri.edu.
Abstract:
We report a new synthesis of the water-soluble compound 1,3,5-trihydroxy-2,4,6-trimethylsulfonic acid (1), which exists in two tautomeric forms (60 : 40::enol%:keto%) and can be used as a proton conductor. Quantum chemical calculations show the importance of intramolecular hydrogen bonding and the presence of implicit MeOH solvent on the relative stabilities of the tautomers. 1 complexes with lanthanides through its sulfonato groups and forms a layered cage-like structure with one intramolecular and two intermolecular hydrogen bonds.
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