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Regio- and stereospecific addition of phosphines to cyanoacetylenes
Authors:Nina K Gusarova  Svetlana I ShaikhudinovaSvetlana N Arbuzova  Tamara I Vakul'skayaBoris G Sukhov  Lidiya M SinegovskayaMikhail V Nikitin  Anastasiya G Mal'kinaNataliya A Chernysheva  Boris A Trofimov
Affiliation:A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences 1, Favorsky Street, Irkutsk 664033, Russian Federation
Abstract:Primary and secondary phosphines add regio- and stereospecifically to phenylcyanoacetylene and 4-hydroxy-4-methylpent-2-ynenitrile under mild conditions to form corresponding functionalized secondary and tertiary phosphines of Z-configuration in 70-91% yield. According to ESR and UV data, the addition of primary phosphines to phenylcyanoacetylene involves a single electron transfer process.
Keywords:cyanoacetylenes   primary phosphines   secondary phosphines   nucleophilic addition   single electron transfer
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