Research output: Contribution to conference - Without ISBN/ISSN › Abstract › peer-review
Research output: Contribution to conference - Without ISBN/ISSN › Abstract › peer-review
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TY - CONF
T1 - Direct observation of the fructofuranosyl oxocarbenium ion
T2 - 245th ACS National Meeting
AU - Akien, Geoffrey
AU - Subramaniam, Bala
PY - 2013/4/10
Y1 - 2013/4/10
N2 - 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.
AB - 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.
M3 - Abstract
Y2 - 7 April 2013 through 12 April 2013
ER -