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Lead tetrabenzoate oxidation of trimethylsilyl enol ethers

โœ Scribed by Rubottom, George M.; Gruber, John M.; Mong, Gary M.


Book ID
126126022
Publisher
American Chemical Society
Year
1976
Tongue
English
Weight
277 KB
Volume
41
Category
Article
ISSN
0022-3263

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Peracid oxidation of trimethylsilyl enol
โœ G.M. Rubottom; M.A. Vazquez; D.R. Pelegrina ๐Ÿ“‚ Article ๐Ÿ“… 1974 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 192 KB

The oxidation of trimethylsilyl enol ethers, L, in hexane solution, with s-chloroperbenzoic acid (MCPBA), followed by treatment of the crude reaction mixture with acid or base, affords a general, high yield method for the specific a-hydroxylation of ketones (ie, acyloin, 2, production)(Equation l)!

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Synthesis of 1,4-diketones in good yields was achieved by the coupling reaction of the trinethylsilyl enol ethers of acetophenone, thiophene or furan with lead tetraacetate in dry dichloromethane and tetrahydrofuran at -78"C.