Reactions of Elemental Phosphorus and Phosphine with Electrophiles in Superbasic Systems: XV. Phosphorylation of Allyl Halides with Elemental Phosphorus |
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| Authors: | 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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| Institution: | (1) Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, Russia;(2) Irkutsk State University, Urkutsk, Russia |
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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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