Reactions of Elemental Phosphorus and Phosphine with Electrophiles in Superbasic Systems: XIV.1 Phosphorylation of 2-Vinylnaphthalene with Elemental Phosphorus and Phosphines in the KOH-DMSO System |
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| Authors: | N K Gusarova S I Shaikhutdinova T I Kazantseva S F Malysheva B G Sukhov N A Belogorlova V I Dmitriev 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, Irkutsk, Russia |
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| Abstract: | Elemental phosphorus (red or white) reacts with 2-vinylnaphthalene while heating at 90-96°C in the superbasic KOH-DMSO system to form 2-(2-naphthyl)ethylphosphine, 2-(2-naphthyl)ethylphosphinic acid, bis2-(2-naphthyl)ethyl]phosphine, bis2-(2-naphthyl)ethyl]phosphine oxide, and tris2-(2-naphthyl)ethyl]phosphine oxide in a total yield of up to 40%. Selective conditions for preparing the tertiary phosphine oxide from white phosphorus and 2-vinylnaphthalene in 58% yield were found. Phosphine and (2-phenylpropyl)phosphine add to 2-vinylnaphthalene in the KOH-DMSO system to form, under certain conditions, corresponding secondary phosphines in high yields. |
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