title: Polymer-mediated cyclodehydration of alditols and ketohexoses.
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.
authors.affiliation: University of Connecticut, Department of Chemistry, Storrs, CT 06269-3060, USA.
authors.forename: Amber
authors.initials: A
authors.lastname: Onorato
authors.forename: Christopher
authors.initials: C
authors.lastname: Pavlik
authors.forename: Michael A
authors.initials: MA
authors.lastname: Invernale
authors.forename: Ian D
authors.initials: ID
authors.lastname: Berghorn
authors.forename: Gregory A
authors.initials: GA
authors.lastname: Sotzing
authors.forename: Martha D
authors.initials: MD
authors.lastname: Morton
authors.forename: Michael B
authors.initials: MB
authors.lastname: Smith
mesh_terms: D006601:Hexoses / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry*; D013402:Sugar Alcohols / Q000737:chemistry*
chemical_list: D006601:Hexoses; D011108:Polymers; D013402:Sugar Alcohols