Journal of Organic Chemistry p. 2559 - 2562 (1987)
Update date:2022-08-11
Topics:
Anelli, Pier Lucio
Biffi, Carlo
Montanari, Fernando
Quici, Silvio
Primary alcohols are quantitatively oxidized to aldehydes in a few minutes at 0 deg C in CH2Cl2-0.35 M aqueous NaOCl in the presence of catalytic amounts of 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxyl (3b).Cocatalysis by Br- and buffering of pH at 8.6 with NaHCO3 are also required.Secondary alcohols are converted to ketones.Further oxidation of aldehydes to carboxylic acids is slow, but the reaction is completed in a few minutes under the same conditions by addition of catalytic amounts of phase-transfer catalyst.All reactions are highly selective.Onlya slight excess of NaOCl is required.The method can be applied to saturated alkyl and aryl alkyl substrates.
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Doi:10.1016/0022-328X(84)80570-7
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