Novel 2-Phosphabicyclo[2.2.2]oct-5-ene Derivatives and Their Use in Phosphinylations

G. Keglevich, János Kovács, T. Körtvélyesi, Gyula Parlagh, T. Imre, K. Ludányi, L. Hegedûs, Miklós Hanusz, Kálmán Simon, Andrea Márton, G. Marosi, L. Tőke

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The [4 + 2] cycloaddition of the double-bond isomers (A and B) of dihydrophosphinine oxide 1 afforded novel phosphabicyclo[2.2.2]oct-5-ene derivates (2-4), formation of which was justified by PM3 semiempirical calculations. The compounds of dimer type (2-4) were utilized in the UV light-mediated fragmentation-related phosphinylation of nucleophiles, especially in that of alcohols. To explore the role of structural modifications on the fragmentation ability, disulfide 5, phosphabicyclooctane 7 obtained by the hydrogenation of 2, and the adduct of dihydrophosphinine oxide 1 with benzoquinone (7) were also synthesized and tested in fragmentation.

Original languageEnglish
Pages (from-to)97-106
Number of pages10
JournalHeteroatom Chemistry
Volume15
Issue number2
DOIs
Publication statusPublished - 2004

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Oxides
Derivatives
Nucleophiles
Cycloaddition
Ultraviolet radiation
Disulfides
Isomers
Dimers
Hydrogenation
Alcohols
benzoquinone

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Novel 2-Phosphabicyclo[2.2.2]oct-5-ene Derivatives and Their Use in Phosphinylations. / Keglevich, G.; Kovács, János; Körtvélyesi, T.; Parlagh, Gyula; Imre, T.; Ludányi, K.; Hegedûs, L.; Hanusz, Miklós; Simon, Kálmán; Márton, Andrea; Marosi, G.; Tőke, L.

In: Heteroatom Chemistry, Vol. 15, No. 2, 2004, p. 97-106.

Research output: Contribution to journalArticle

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AU - Keglevich, G.

AU - Kovács, János

AU - Körtvélyesi, T.

AU - Parlagh, Gyula

AU - Imre, T.

AU - Ludányi, K.

AU - Hegedûs, L.

AU - Hanusz, Miklós

AU - Simon, Kálmán

AU - Márton, Andrea

AU - Marosi, G.

AU - Tőke, L.

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AB - The [4 + 2] cycloaddition of the double-bond isomers (A and B) of dihydrophosphinine oxide 1 afforded novel phosphabicyclo[2.2.2]oct-5-ene derivates (2-4), formation of which was justified by PM3 semiempirical calculations. The compounds of dimer type (2-4) were utilized in the UV light-mediated fragmentation-related phosphinylation of nucleophiles, especially in that of alcohols. To explore the role of structural modifications on the fragmentation ability, disulfide 5, phosphabicyclooctane 7 obtained by the hydrogenation of 2, and the adduct of dihydrophosphinine oxide 1 with benzoquinone (7) were also synthesized and tested in fragmentation.

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