Studies on the Conversions of Diols and Cyclic Ethers. Part 48. Dehydration of alcohols and diols on the action of dimethylsulfoxide

Árpád Molnár, M. Bartók

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12 Citations (Scopus)

Abstract

The transformations of 13 alcohols and 13 diols in the presence of a small amount dimethylsulfoxide (1/16 mol) were studied. Relationships were found between the type of the hydroxy compound and the selectivity of the transformation, and conclusions were drawn regarding the transformation mechanism. The ether formation observed with certain alcohols proceeds via a carbenium cation. The reaction conditions applied were found suitable for inducing water elimination from the ditertiary 1,2‐ and 1,3‐diols (pinacol rearrangement, 1,2‐elimination). From the 1,4‐ and 1,5‐diols the corresponding oxacycloalkanes can be obtained in good yield. Cyclodehydration occurs by intramolecular nucleophilic substitution, via a concerted mechanism. The effect of DMSO is exerted directly, and protoncatalysis occurs simultaneously.

Original languageEnglish
Pages (from-to)389-398
Number of pages10
JournalHelvetica Chimica Acta
Volume64
Issue number2
DOIs
Publication statusPublished - 1981

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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