Synthesis and stereochemistry of 1,3,2-oxazaphosphorino [4,3-A]isoquinolines

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1,3,2-Oxazaphosphorino[4,3-A]isoquinolines 8a,b, 9a,b and 10a were synthesized by the reactions of homocalycotomine 7 with appropriate dichlorophosphorus derivatives, such as phenylphosphonic dichloride, bis(2-chloroethyl)phosphonic dichloride or phosphoryl chloride. In spite of the blocking effect of the connecting isoquinoline ring system, the oxazaphosphorinane moiety exists as a chair-twist equilibrium, where the conformer ratios are strongly dependent on the P-4 configuration and the stereoelectronic properties of the substituents. (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)119-125
Number of pages7
JournalJournal of Molecular Structure
Issue number2-3
Publication statusPublished - Nov 7 2000



  • Conformational equilibria
  • Crystal structure
  • Oxazaphosphorinane

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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