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Selenium-catalyzed Conversion Of Methyl Ketones Into .alpha.-keto Acetals

M. Tiecco, L. Testaferri, M. Tingoli, D. Bartoli
Published 1990 · Chemistry

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The reaction of methyl ketones with catalytic amounts of diphenyl diselenide and an excess of ammonium peroxydisulfate in methanol proceeds smoothly to afford α-keto acetals in good yield. In some cases reaction yields were increased by using stoichiometric amounts of PhSeSePh. It is suggested that the oxidation of PhSeSePh by (NH 4 ) 2 S 2 O 8 produces a very electrophilic phenylselenenylating agent that effects the methoxyselenenylation of the methyl ketones. The addition products so formed react with (NH 4 ) 2 S 2 O 8 to afford the methoxydeselenenylation products; the phenylselenenylating agent is thus regenerated. Thus, the entire process can be effected in one pot and with catalytic amounts of PhSeSePh



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