Polymer-mediated cyclodehydration of alditols and ketohexoses

Amber Onorato, Christopher Pavlik, Michael A. Invernale, Ian D. Berghorn, Gregory A. Sotzing, Martha D. Morton, Michael B. Smith

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

The polymer PEDOT+ (1 or 2) mediates a cyclodehydration reaction with alditols 3, 5, 7, 9, in hydrocarbon solvents, to give cyclic ethers 4, 6, 8, or 10, respectively, in high yield with a trivial isolation protocol. Polymers 1 or 2 also mediate the cyclodehydration of ketohexoses such as D-fructose, but not aldohexoses, to the important industrial intermediate 5-hydroxymethylfurfural (17), under milder conditions when compared to reactions mediated by mineral acids. A cascade reaction with ketohexoses is observed in toluene via cyclodehydration followed by Friedel-Crafts alkylation of the initially formed benzylic alcohol to give 16.

Original languageEnglish (US)
Pages (from-to)1662-1670
Number of pages9
JournalCarbohydrate Research
Volume346
Issue number13
DOIs
StatePublished - Sep 2011

Keywords

  • 5-Hydroxymethylfurfural
  • Alditols
  • Anhydroalditols
  • Cyclodehydration
  • Ketohexoses
  • PEDOT

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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    Onorato, A., Pavlik, C., Invernale, M. A., Berghorn, I. D., Sotzing, G. A., Morton, M. D., & Smith, M. B. (2011). Polymer-mediated cyclodehydration of alditols and ketohexoses. Carbohydrate Research, 346(13), 1662-1670. https://doi.org/10.1016/j.carres.2011.04.017