Ring-opening of cyclic ethers with carbon–carbon bond formation by Grignard reagents

Stig Holden Christensen, Torkil Holm, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review


The ring-opening of cyclic ethers with concomitant C–C bond formation was studied with a number of Grignard reagents. The transformation was performed in a sealed vial by heating to ∼160 °C in an aluminum block or at 180 °C in a microwave oven. Good yields of the product alcohols were obtained with allyl- and benzylmagnesium halides when the ether was tetrahydrofuran or 3,3-dimethyloxetane. Lower yields were obtained with substituted tetrahydrofurans while no ring-opening was observed with tetrahydropyran. Only highly reactive allyl and benzyl Grignard reagents participated in the transformation while no reaction occurred with other alkylmagnesium halides.
Original languageEnglish
Issue number33
Pages (from-to)4942-4946
Publication statusPublished - 2014


  • C–C bond formation
  • Cyclic ether
  • Grignard reagent
  • Nucleophilic substitution
  • Ring-opening


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