Evaluation of C-trialkylsilyl enol and thioenol ethers as intermediates in the synthesis of acylsilanes |
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Authors: | Catherine Hammaecher Jean-Philippe Bouillon |
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Affiliation: | UMR 6519 ‘Réactions Sélectives et Applications’, CNRS-Université de Reims Champagne-Ardenne, B. P. 1039, 51687 REIMS Cedex 2, France |
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Abstract: | C-silyl enol ethers or thioenol ethers have been prepared by a Peterson reaction, as intermediates for acylsilane synthesis. Bis(trialkylsilyl)(methoxy)- or -(methylsulfanyl)methanes bearing identical or different trialkylsilyl groups were used as starting materials in order to assess the selectivity of the Peterson elimination step. A good selectivity was observed only with ethers bearing the TMS and TBDMS groups. However, there is no practical interest to use such reagents owing to the difficulty to obtain them in correct yields. Bis(trimethylsilyl)(methylsulfanyl)methane proved to be a good reagent for the preparation of C-silyl thioenol ethers, which are hydrolyzed under classical acid conditions to give acylsilanes in fair overall yields. This convenient procedure was extended to the synthesis of bis(acylsilanes). |
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Keywords: | Organosilicon Peterson olefination Acylsilane Enol ether Thioenol ether |
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