A versatile building block for the synthesis of substituted cyclopropanephosphonic acid esters

László Töke, Zsuzsa M. Jászay, Imre Petneházy, György Clementis, Györgyi D. Vereczkey, István Kövesdi, Antal Rockenbauer, Katalin Kováts

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Abstract

By the effect of iodine, solid K2CO3 and a lipophilic quaternary ammonium salt phosphonoacetic acid allylic esters 4 were converted to cyclopropanephosphonic acid derivatives anellated to a five membered lactone ring 6 serving as good starting material for biologically active products. The reaction of cyclopropanation has been assumed to proceed by SET induced radical type elemental steps. Direct evidences were given by ESR for the 6-endo regioselectivity in the closure of electrophilic radical 11. An interesting and new exchange reaction of phosphonic ester moiety by iodine is also observed.

Original languageEnglish
Pages (from-to)9167-9178
Number of pages12
JournalTetrahedron
Volume51
Issue number33
DOIs
Publication statusPublished - Aug 14 1995

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Töke, L., Jászay, Z. M., Petneházy, I., Clementis, G., Vereczkey, G. D., Kövesdi, I., Rockenbauer, A., & Kováts, K. (1995). A versatile building block for the synthesis of substituted cyclopropanephosphonic acid esters. Tetrahedron, 51(33), 9167-9178. https://doi.org/10.1016/0040-4020(95)00522-A