Lactones and ketal-lactones prepared from AlCl3-catalyzed reactions of cycloalkenedicarboxylic anhydrides with toluene

József A. Szabó, Pál Sohár, Zsolt Böcskei, Géza Stájer, Gábor Bernáth

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

By means of the AlCl3-catalyzed reactions of (bi)cycloalkene dianhydrides with toluene, lactones and tricyclic or tetracyclic ketal- lactones were prepared. The nature of the products obtained depends greatly on the solvent, the molar ratio and sequence of addition of the reactants, and the temperature. For the ketal-lactone, AlCl3 promotes the formation of the cyclotautomer of the γ-ketocarboxylic acid intermediate, and the α- hydroxylactone then adds to the unsaturated carbon bond. The endo-aroyl group of the norbornane lactone can readily be transformed to an exo-group at elevated temperature. The structures were established by NMR and X-ray measurements.

Original languageEnglish
Pages (from-to)1564-1568
Number of pages5
JournalSynthesis
Issue number9
Publication statusPublished - Jan 1 1999

Keywords

  • AlCl-catalyzed reactions
  • Arachno-structure compounds
  • Ketal-lactones
  • Lactones

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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