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intramolecular michael and anti-michael additions of thiolate to conjugated acetylenic ketones

✍ Scribed by Wolf-Dieter Rudorf; Ralf Schwarz


Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
267 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis


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,


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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