Synthesis of the spiro derivatives of 1,2-oxaphosphetes by [2+2] cycloaddition of cyclic 1-(2,4,6-triisopropylphenyl)phosphine oxides with dimethyl acetylenedicarboxylate

György Keglevich, Henrietta Forintos, György Miklós Keseru, László Hegedus, László Toke

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Members of a new heterocyclic family, 1,2-oxaphosphetes were prepared by the unexpected [2+2] cycloaddition of the P = O group of 1-(2,4,6- triisopropylphenyl) P-heterocycles with the acetylene moiety of dimethyl acetylenedicarboxylate. The new oxaphosphetes are spiro derivatives of the starting heterocycles and exhibit a phosphorus atom with trigonal bipyramidal geometry. PM3 semiempirical calculations justified the novel reaction path and suggested a stepwise reaction mechanism. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)4823-4828
Number of pages6
JournalTetrahedron
Volume56
Issue number27
DOIs
Publication statusPublished - Jun 30 2000

Keywords

  • Cycloaddition
  • Mechanism
  • P-heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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