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

doi:10.1016/j.carres.2011.04.017

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 journal › Article › peer-review

15 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 language	English (US)
Pages (from-to)	1662-1670
Number of pages	9
Journal	Carbohydrate Research
Volume	346
Issue number	13
DOIs	https://doi.org/10.1016/j.carres.2011.04.017
State	Published - Sep 2011
Externally published	Yes

Keywords

5-Hydroxymethylfurfural
Alditols
Anhydroalditols
Cyclodehydration
Ketohexoses
PEDOT

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.carres.2011.04.017

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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.",

keywords = "5-Hydroxymethylfurfural, Alditols, Anhydroalditols, Cyclodehydration, Ketohexoses, PEDOT",

author = "Amber Onorato and Christopher Pavlik and Invernale, {Michael A.} and Berghorn, {Ian D.} and Sotzing, {Gregory A.} and Morton, {Martha D.} and Smith, {Michael B.}",

year = "2011",

month = sep,

doi = "10.1016/j.carres.2011.04.017",

language = "English (US)",

volume = "346",

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journal = "Carbohydrate Research",

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TY - JOUR

T1 - Polymer-mediated cyclodehydration of alditols and ketohexoses

AU - Onorato, Amber

AU - Pavlik, Christopher

AU - Invernale, Michael A.

AU - Berghorn, Ian D.

AU - Sotzing, Gregory A.

AU - Morton, Martha D.

AU - Smith, Michael B.

PY - 2011/9

Y1 - 2011/9

N2 - 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.

AB - 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.

KW - 5-Hydroxymethylfurfural

KW - Alditols

KW - Anhydroalditols

KW - Cyclodehydration

KW - Ketohexoses

KW - PEDOT

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AN - SCOPUS:80052668106

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JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 13

ER -

Polymer-mediated cyclodehydration of alditols and ketohexoses

Abstract

Keywords

ASJC Scopus subject areas

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