1. Polymer-mediated cyclodehydration of alditols and ketohexoses
- Author
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Onorato, Amber, Pavlik, Christopher, Invernale, Michael A., Berghorn, Ian D., Sotzing, Gregory A., Morton, Martha D., and Smith, Michael B.
- Subjects
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POLYMERS , *CHEMICAL reactions , *MONOSACCHARIDES , *SOLVENTS , *FRIEDEL-Crafts reaction , *ALKYLATION , *TOLUENE - Abstract
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. [Copyright &y& Elsevier]
- Published
- 2011
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