The cis-trans isomerisation of homologous 2-hydroxycycloalkanecarboxylic acids under basic conditions

Cs Zsuzsanna Gyarmati, István Pálinkó, Attila Bokros, A. Tamás Martinek, Gábor Bernáth

Research output: Contribution to journalArticle

Abstract

The cis→trans isomerisation of homologous 2- hydroxycycloalkanecarboxylic acids in strongly basic aqueous solution was studied starting from the cis isomers. It was found that the cyclopentane, cyclohexane and cycloheptane homologues afforded synthetically useful amounts of the trans acids and the procedure resulted in relatively small quantities of the corresponding olefinic acids. In contrast, the isomerisation of the cis-2-hydroxycyclooctanecarboxylic acid produced roughly equal amounts of the cis and trans isomers and the 1-cyclooctenecarboxylic acid at equilibrium. Molecular modelling with the PM3 semiempirical method of the reactants, products and the intermediates applying explicit water molecules as reaction medium gave a fair estimate for the rate sequence of the idealised (dehydration-free) isomerisation reactions in aqueous base solution.

Original languageEnglish
Pages (from-to)1792-1795
Number of pages4
JournalChinese Journal of Chemistry
Volume24
Issue number12
DOIs
Publication statusPublished - Dec 1 2006

Keywords

  • Base catalysis
  • Geometric isomerisation
  • Molecular modelling
  • Reaction mechanism

ASJC Scopus subject areas

  • Chemistry(all)

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