Reactions of Elemental Phosphorus and Phosphines with Electrophiles in Superbasic Systems: XIII. Phosphorylation of Phenylacetylene with Active Modifications of Elemental Phosphorus |
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Authors: | Gusarova N. K. Sukhov B. G. Malysheva S. F. Kazantseva T. I. Smetannikov Yu. V. Tarasova N. P. Trofimov B. A. |
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Affiliation: | (1) Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, Russia |
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Abstract: | Phosphorylation of phenylacetylene with white or activated red phosphorus (prepared from white phosphorus under the action of ionizing radiation) occurs in KOH-DMSO or KOH-HMPA systems with heat evolution and stereoselective formation of Z isomers of tristyrylphosphine and -phosphine oxide in yields of 48-49% and 10-15%, respectively. Under the comparable conditions the commercial red phosphorus is considerably less reactive toward phenylacetylene: The total yield of the above-mentioned products is 5%. |
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