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Direct observation of the fructofuranosyl oxocarbenium ion: a critical intermediate in the valorization of carbohydrates

Research output: Contribution to conference - Without ISBN/ISSN › Abstract › peer-review

Published
Publication date10/04/2013
<mark>Original language</mark>English
Event245th ACS National Meeting - Louisiana, New Orleans, United States
Duration: 7/04/2013 → 12/04/2013

Conference

Conference245th ACS National Meeting
Country/TerritoryUnited States
CityNew Orleans
Period7/04/13 → 12/04/13

Abstract

We report the first direct observation of the fructofuranosyl oxocarbenium ion by low temperature NMR, a critical intermediate in the valorization of carbohydrates. Due to the relatively high reactivity of fructose, protected fructoses were combined at low temperature with a suitable superacid. While the analogous (secondary) glycopyranosyl cation has so far eluded detection, the increased stability of the tertiary fructofuranosyl oxocarbenium ion is probably responsible for its prolonged lifetime in solution.