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.

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

245th National Meeting (2013)

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