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

G. Keglevich, Henrietta Forintos, György Miklós Keseru, L. Hegedûs, L. Tőke

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
Publication statusPublished - Jun 30 2000

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phosphine
Acetylene
Cycloaddition
Cycloaddition Reaction
Phosphorus
Oxides
Derivatives
Atoms
Geometry
acetylenedicarboxylic acid dimethyl ester

Keywords

  • Cycloaddition
  • Mechanism
  • P-heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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. / Keglevich, G.; Forintos, Henrietta; Keseru, György Miklós; Hegedûs, L.; Tőke, L.

In: Tetrahedron, Vol. 56, No. 27, 30.06.2000, p. 4823-4828.

Research output: Contribution to journalArticle

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AU - Hegedûs, L.

AU - Tőke, L.

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