Reactions of uracils, 181: Reaction of 5-formyl-1, 3-dimethylbarbituric acid and 5-formyl-l, 3, 6-trimethyluracil with ethoxycarbonylmethylenetriphenylphosphorane

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Abstract

Ethoxycarbonylmethylenetriphenylphosphorane (2) reacts with 5-formyl-l, 3, 6-trimethyluracil (1c) in the expected way to afford the acrylate 3c, while with 5-formyl-l, 3-dimethylbarbituric acid (1b) a novel phosphorus ylide/phosphorane 4 is obtained (X-ray analysis). The temperature dependent NMR spectra and the mechanism of formation are discussed.

Original languageEnglish
Pages (from-to)323-328
Number of pages6
JournalPhosphorus, Sulfur, and Silicon and the Related Elements
Volume63
Issue number3-4
DOIs
Publication statusPublished - Dec 1 1991

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Keywords

  • 5-Formyl-l, 3-dimethylbarbituric acid
  • 5-formyl-l, 3, 6-trimethyluracil
  • Wittig reaction; phosphorus ylide
  • ethoxycarbonylmethylenetriphenylphosphorane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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