Aluminum chloride catalyzed stereo- and regiospecific allylsilylation of alkynes: a convenient route to silyldienes
| Autor: | Youngkyu Do, Eunkee Hong, Joon Soo Han, Seung Ho Yeon, Il Nam Jung |
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| Rok vydání: | 1995 |
| Předmět: |
Allylic rearrangement
Aluminium chloride Silylation Trimethylsilyl Chemistry organic chemicals Organic Chemistry food and beverages Triple bond Biochemistry Medicinal chemistry Catalysis Inorganic Chemistry chemistry.chemical_compound Phenylacetylene Materials Chemistry medicine Physical and Theoretical Chemistry Diphenylacetylene medicine.drug |
| Zdroj: | Journal of Organometallic Chemistry. 499:159-165 |
| ISSN: | 0022-328X |
| DOI: | 10.1016/0022-328x(95)00323-i |
| Popis: | Allyltrimethylsilane reacts with phenylalkynes in the presence of aluminium chloride catalyst under mild conditions to afford silylphenyldienes in moderate yield. In this allylsilylation reaction, the silyl group adds regioselectively to the terminal carbon and the allyl group to the inner carbon of the triple bond. The allylsilylation of phenylacetylene gives the allylsilylated product having the silyl and allyl groups in the cis -position, while diphenylacetylene gives the trans product. The allylic inversion was also observed in the allylsilylation with the stereohomogeneous ( Z )-crotyltrimethylsilane. These results are consistent with the initial formation of trimethylsilyl cation intermediate and a stepwise process of allylsilylation. |
| Databáze: | OpenAIRE |
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