The unexpected formation of a dihydroisobenzofuran derivative from the addition of a Grignard reagent to a 1,3-indanedione

James Vile, Mariolino Carta, C. Grazia Bezzu, James Dee, Neil B. McKeown

Research output: Contribution to journalArticlepeer-review

Abstract

Despite good literature precedents, the addition of excess 2-biphenylmagnesium bromide to 4,5-dimethoxy-1,3-indanedione, followed by acid work-up, did not give the desired diol precursor to an Organic Molecule of Intrinsic Microporosity. Instead a dihydroisobenzofuran derivative was isolated in moderate yield and its structure characterised fully by single crystal X-ray crystallography. It is suggested that this product is formed by sequential Grignard addition, retro-aldol reaction, a second Grignard addition and acid-mediated formation of the dihydroisobenzofuran ring.

Original languageEnglish
Pages (from-to)190-195
Number of pages6
JournalARKIVOC
Volume2012
Issue number7
DOIs
Publication statusPublished - 2012

Keywords

  • Grignard reagent
  • retro aldol
  • 1,3-indanedione
  • intrinsic microporosity
  • X-ray crystallography
  • INTRINSIC MICROPOROSITY PIMS
  • POLYMERS

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