Regio- and stereospecific addition of phosphines to cyanoacetylenes
โ Scribed by Nina K Gusarova; Svetlana I Shaikhudinova; Svetlana N Arbuzova; Tamara I Vakul'skaya; Boris G Sukhov; Lidiya M Sinegovskaya; Mikhail V Nikitin; Anastasiya G Mal'kina; Nataliya A Chernysheva; Boris A Trofimov
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 147 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0040-4020
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โฆ Synopsis
Primary and secondary phosphines add regio-and stereospecifically to phenylcyanoacetylene and 4-hydroxy-4-methylpent-2ynenitrile 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.
๐ SIMILAR VOLUMES
Secondary phosphines 1-3 react readily with N-vinylpyrroles 4 and 5 under radical initiation to give regiospecifically anti-Markovnikov adducts, diorganyl-2-(1-pyrrolyl)ethylphosphines 6a-d, highly reactive building blocks for organic synthesis, in 88-91% yields.
Mono-7-substituted-1,3,5-cycloheptatrienes permit two opportunities for stereospecificity beyond those traditionally envisaged for Diels-Alder addition.(l) .