2,4,6-trialkylphenyl-2H-phospholes from slightly aromatic 1H-phospholes and their use in [4 + 2] cycloaddition reactions

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Abstract

1-(2,4,6-Trialkylphenyl) phosphates 1a,b possess a moderate aromatic character. Despite of that they underwent a sigmatropic rearrangement at 150°C to afford 2H-phospholes 2a,b which by trapping with tolane, or in reaction with another unit of 2 gave [4 + 2] cycloadducts 3a,b, or in a reversible reaction, dimer 6, respectively. Dedimerization of species 6 at 150°C in the presence of tolane, or at 0°C under oxidative circumstances, led to 1-phosphanorbornadiene 3a, or phosphole oxide dimer 8, respectively.

Original languageEnglish
Pages (from-to)316-319
Number of pages4
JournalHeteroatom Chemistry
Volume14
Issue number4
DOIs
Publication statusPublished - 2003

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Cycloaddition
Dimers
Oxides
Phosphates

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "2,4,6-trialkylphenyl-2H-phospholes from slightly aromatic 1H-phospholes and their use in [4 + 2] cycloaddition reactions",
abstract = "1-(2,4,6-Trialkylphenyl) phosphates 1a,b possess a moderate aromatic character. Despite of that they underwent a sigmatropic rearrangement at 150°C to afford 2H-phospholes 2a,b which by trapping with tolane, or in reaction with another unit of 2 gave [4 + 2] cycloadducts 3a,b, or in a reversible reaction, dimer 6, respectively. Dedimerization of species 6 at 150°C in the presence of tolane, or at 0°C under oxidative circumstances, led to 1-phosphanorbornadiene 3a, or phosphole oxide dimer 8, respectively.",
author = "G. Keglevich and Ren{\'a}ta Farkas and T. Imre and K. Lud{\'a}nyi and A. Sz{\"o}ll{\"o}sy and L. Tőke",
year = "2003",
doi = "10.1002/hc.10151",
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T1 - 2,4,6-trialkylphenyl-2H-phospholes from slightly aromatic 1H-phospholes and their use in [4 + 2] cycloaddition reactions

AU - Keglevich, G.

AU - Farkas, Renáta

AU - Imre, T.

AU - Ludányi, K.

AU - Szöllösy, A.

AU - Tőke, L.

PY - 2003

Y1 - 2003

N2 - 1-(2,4,6-Trialkylphenyl) phosphates 1a,b possess a moderate aromatic character. Despite of that they underwent a sigmatropic rearrangement at 150°C to afford 2H-phospholes 2a,b which by trapping with tolane, or in reaction with another unit of 2 gave [4 + 2] cycloadducts 3a,b, or in a reversible reaction, dimer 6, respectively. Dedimerization of species 6 at 150°C in the presence of tolane, or at 0°C under oxidative circumstances, led to 1-phosphanorbornadiene 3a, or phosphole oxide dimer 8, respectively.

AB - 1-(2,4,6-Trialkylphenyl) phosphates 1a,b possess a moderate aromatic character. Despite of that they underwent a sigmatropic rearrangement at 150°C to afford 2H-phospholes 2a,b which by trapping with tolane, or in reaction with another unit of 2 gave [4 + 2] cycloadducts 3a,b, or in a reversible reaction, dimer 6, respectively. Dedimerization of species 6 at 150°C in the presence of tolane, or at 0°C under oxidative circumstances, led to 1-phosphanorbornadiene 3a, or phosphole oxide dimer 8, respectively.

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U2 - 10.1002/hc.10151

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