The synthesis of olefins from β-ketosilanes
✍ Scribed by Paul F. Hudrlik; David Peterson
- Publisher
- Elsevier Science
- Year
- 1972
- Tongue
- French
- Weight
- 155 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Sew Jerse:. C3903 Like acyloxysilanes, 1 p-ketosilanes can react with a nucleophile in two ways.
We have found that the reaction of a S-ketosilane with alkoxide gives a product resulting from displacement at the silicon atom, while the reactions with Grignard reagents and with organolithium compounds give only products re-2 sulting from addition to the carbonyl group.
Since the p-hydroxyalkylsilanes B formed in the latter reactions can be converted into olefins, the process serves as a potential synthetic route to these compounds.
📜 SIMILAR VOLUMES
The reaction of cc-silyl esters with an excess of a Grignard reagent leads to B-ketosilanes in good yield.
A convenient, novel synthesis of b-ketosilanes based on (Z)-1-bromo-1-alkenylboronate esters is developed. a-Bromo-(Z)-1-alkenylboronate esters readily available using literature procedures smoothly undergo a reaction with trimethylsilylmethyllithium in tetrahydrofuran to provide the corresponding `
Reductive elimination of groups including sulfur from organosulfur compounds has been extensively studied' from the viewpoint of organic synthesis.