Transformation of 1,3-, 1,4- and 1,5-diols over perfluorinated resinsulfonic acids (Nafion-H)

Imre Bucsi, Árpád Molnár, Mihály Bartók, George A. Olah

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Abstract

The transformations of 1,3-, 1,4- and 1,5-diols over perfluorinated resinsulfonic acids (Nafion-H) were studied and correlations were examined between the structure of the investigated diols, the possible transformation directions and the catalytic properties of Nafion-H. Comparisons were also made between the catalytic properties of Nafion-H and zeolites. The characteristic transformations of 1,3-diols depend on their structure. 1,3-Propanediol undergoes dehydration via 1,2-elimination and yields oligomers via intermolecular dehydration. 1,3-Diols with an alkyl substituent on the carbon between those bearing the OH groups undergo 1,2-elimination yielding unsaturated alcohols and dienes, and give carbonyl compounds via the loss of water and hydride shifts analogous to the pinacol rearrangement. The strong acidity of Nafion-H and the lack of strong basic sites are advantageous for the latter reaction. 1,3-Diols with two substituents at this position mainly yield fragmentation products. Stereoselective cyclodehydration to the corresponding oxacycloalkanes is the characteristic transformation of 1,4- and 1,5-diols over Nafion-H.

Original languageEnglish
Pages (from-to)3319-3326
Number of pages8
JournalTetrahedron
Volume51
Issue number11
DOIs
Publication statusPublished - Mar 13 1995

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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