In the nucleophilic addition on conjugated olefinic ketones (enones), stereoelectronic effects predict that the intermediate enolate should first be generated in a conformation where the newly formed bond is parallel with the II system of the enolatel. Stereoelectronic parameters predict also that t
Intramolecular Michael addition of cyclic β-ketoester on conjugated acetylenic ketone.
✍ Scribed by Jean-François Lavallée; Gilles Berthiaume; Pierre Deslongchamps; Fritz Grein
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 216 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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The reaction of acetglenic ketones 1 with carbon disulfide in the basic system sodium hydride/dimethylformamide and subsequent intramolecular cgclization to 4H-thiopyran-J-ones 2 and 3(2H)-thiophenones 2 are reported,
The enolates of cyclic ~-ketoesters react with electrophilic acetylenes to give the corresponding Michael adducts in good yields when the reaction is performed in acetone in the presence of catalytic amounts of K2CO 3. The Michael adducts resulting from ethynylmethylketone, when refluxed in toluene