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Regiospecific Synthesis of α-Diones, α,α-Dialkoxyketones and α-Alkoxy-α-sulfenylated Ketones

✍ Scribed by Kourosch Abbaspour Tehrani; Marc Boeykens; Vladimir I. Tyvorskii; Oleg Kulinkovich; Norbert De Kimpe

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
142 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐA convenient synthesis of a-diones and their monoprotected acetals, i.e. a-ketoacetals, was developed by mercury induced solvolysis of regiospeci®cally formed a-chloro-a-(alkylthio)ketones. Analogously, a-alkoxy-a-sulfenylated ketones were formed when reacting a-chloro-a-sulfenylated ketones with an alkaline alcoholic medium. a-Alkoxy-a-sulfenylated ketones themselves could be transformed into a-diones or a-ketoacetals, which in turn were hydrolyzed under anhydrous conditions into the corresponding a-diones.

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