Russian Chemical Bulletin p. 918 - 923 (1998)
Update date:2022-08-11
Topics:
Akhrem
Churilova
Orlinkov
Afanas'eva
Vitt
Petrovskii
A new approach to the direct synthesis of ketones from alkanes or cycloalkanes (RH), CO, and silanes is proposed. Ketones were obtained in 50-97% yields from propane, butane, cyclopentane, cyclohexane, and methylcyclopentane on treatment with CO and silanes (Me4Si, Et4Si, or m-and p-XC6H4SiMe3, where X = Cl, Me, OMe) in the presence of CX4 · 2AlBr3 (X = Br, Cl) superacids at 0 °C. The reactions with m-and p-XC6H4SiMe3 (X = Cl, Me) occur regioselectively to give m-ketones from m-silanes and p-ketones from p-silanes. However, the only product, p-MeOC6H4COR, is formed both from m-and p-MeOC6H4SiMe3. The reaction of Cyclo-C5H9CO+ with BzSiMe3 results in an organosilicon ketone, Me3SiCH2QH4COC5H9, while in the presence of an excess of an acylating system (after alcoholysis), Me2Si(OR′)CH2C6H4COR is formed.
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