Synthesis and Spectroscopic Investigation of Some Dimeric Coumarin and Furanocoumarin Models

M. H.A. Elgamal, N. M.M. Shalaby, M. A. Shaban, H. Duddeck, B. Mikhova, A. Simon, G. Tóth

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Abstract

The synthesis of some dimeric coumarin and furanocoumarin models and their structure elucidation by 1H NMR, 13C NMR, and mass spectroscopy is presented. In the presence of moisture some aldehydes are accompanied by their hydrates. Methoxy signal doubling in the presence of a chiral lanthanide shift reagent proves the dimeric nature of compound 8. In the mass spectra, heterolytic cleavage of the O-C linkage was noticed which is a rare fragmentation in the case of aromatic ethers.

Original languageEnglish
Pages (from-to)701-712
Number of pages12
JournalMonatshefte fur Chemie
Volume128
Issue number6-7
DOIs
Publication statusPublished - Jan 1 1997

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Keywords

  • Aldehyde hydrates
  • Bis-Coumarins
  • Bis-Furanocoumarins
  • C NMR
  • Chirality
  • Fragmentation
  • H NMR
  • Mass spectrometry

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Elgamal, M. H. A., Shalaby, N. M. M., Shaban, M. A., Duddeck, H., Mikhova, B., Simon, A., & Tóth, G. (1997). Synthesis and Spectroscopic Investigation of Some Dimeric Coumarin and Furanocoumarin Models. Monatshefte fur Chemie, 128(6-7), 701-712. https://doi.org/10.1007/BF00807602