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Reactions of Elemental Phosphorus and Phosphine with Electrophiles in Superbasic Systems: XV. Phosphorylation of Allyl Halides with Elemental Phosphorus

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Abstract

Elemental phosphorus (red or white) reacts with allyl chloride and allyl bromide in a two-phase system aqueous KOH-organic solvent to form tertiary symmetrical and mixed phosphine oxides among which tris(prop-2-enyl)-, bis(prop-2-enyl)[(E)-prop-1-enyl]-, bis(prop-2-enyl)[(Z)-prop-1-enyl]-, (prop-2-enyl)[(E)-prop-1-enyl][(Z)-prop-1-enyl]-, bis[(E)-prop-1-enyl](prop-2-enyl)-, bis[(Z)-prop-1-enyl](prop-2-enyl)-, tris-[(E)-prop-1-enyl]-, and bis[(E)-prop-1-enyl][(Z)-prop-1-enyl]phosphine oxides were identified. The conditions (room temperature, 60% aqueous KOH-dioxane) allowing preparation from white phosphorus and allyl bromide of tris(prop-2-enyl)- and bis(prop-2-enyl)[(E)-prop-1-enyl]phosphine oxides as major products in the total yield of up to 96% were found.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, Russia

    S. F. Malysheva, B. G. Sukhov, N. K. Gusarova, A. V. Afonin, S. I. Shaikhudinova, T. I. Kazantseva, N. A. Belogorlova, V. A. Kuimov, G. V. Plotnikova & B. A. Trofimov

  2. Irkutsk State University, Urkutsk, Russia

    S. F. Malysheva, B. G. Sukhov, N. K. Gusarova, A. V. Afonin, S. I. Shaikhudinova, T. I. Kazantseva, N. A. Belogorlova, V. A. Kuimov, G. V. Plotnikova & B. A. Trofimov

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  1. S. F. Malysheva
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Malysheva, S.F., Sukhov, B.G., Gusarova, N.K. et al. Reactions of Elemental Phosphorus and Phosphine with Electrophiles in Superbasic Systems: XV. Phosphorylation of Allyl Halides with Elemental Phosphorus. Russian Journal of General Chemistry 74, 1091–1096 (2004). https://doi.org/10.1023/B:RUGC.0000045870.75005.72

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  • DOI: https://doi.org/10.1023/B:RUGC.0000045870.75005.72

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