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Reaction of Vinylpyridines with Active Modifications of Elemental Phosphorus in KOH/DMSO

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The phosphorylation of 2-vinyl- and 4-vinylpyridines by white phosphorus and active modifications of red phosphorus (obtained by thermal polymerization of white phosphorus in the presence of graphite or the action of ionizing radiation in benzene) in the KOH/DMSO superbase system at room temperature leads to the formation of tris[2-(2-pyridyl)ethyl]- and tris[2-(4-pyridyl)ethyl]phosphine oxides in 58-72% yield. These oxides are promising ligands for design of metal complex catalysts. These vinylpyridines react less efficiently with ordinary red phosphorus and the yield of the corresponding tris(2-pyridylethyl)phosphine oxides does not exceed 10%.

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Authors and Affiliations

  1. Irkutsk Institute of Chemistry, Siberian Branch of Russian Academy of Sciences, 664033, Russia

    N. K. Gusarova, S. I. Shaikhudinova, T. I. Kazantseva, B. G. Sukhov, V. I. Dmitriev, L. M. Sinegovskaya, Yu. V. Smetannikov, N. P. Tarasova & B. A. Trofimov

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  1. N. K. Gusarova
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  2. S. I. Shaikhudinova
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  3. T. I. Kazantseva
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  4. B. G. Sukhov
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  5. V. I. Dmitriev
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  6. L. M. Sinegovskaya
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  7. Yu. V. Smetannikov
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  8. N. P. Tarasova
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  9. B. A. Trofimov
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Gusarova, N.K., Shaikhudinova, S.I., Kazantseva, T.I. et al. Reaction of Vinylpyridines with Active Modifications of Elemental Phosphorus in KOH/DMSO. Chemistry of Heterocyclic Compounds 37, 576–580 (2001). https://doi.org/10.1023/A:1011604621535

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  • DOI: https://doi.org/10.1023/A:1011604621535

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