Pyridine assisted oxidations of alcohols to carbonyl compounds by means of 3-car☐ypyridinium dichromate (ndc) reagent

Add time:08/03/2019    Source:sciencedirect.com

3-Car☐ypyridinium dichromate (NDC),readly prepared from nicotinic acid and chromium trioxide, is an efficient reagent for the oxidation of alcohols into carbonyl compounds in the presence of pyridine. The optimum molar ratio substrate:reagent:pyridine to ensure complete oxidation of starting material in a short reaction time was found 1:2.5:20 respectively. A brief comparison between this reagent and pyridinium dichromate (PDC) is made. In contrast to the PDC reagent, NDC allows selective oxidation between benzylic alcohols and aliphatic alcohols. The NDC-pyridine system has been successfully extended to the oxidation of N-(2-hidroxy-2-phenyl or 2-methylethyl)-β-lactams into their corresponding carbonyl compounds as N-H azetidin-2-one precursors. In contrast, primary N-(2-hydroxyethyl)-β-lactams upon treatment with this reagent system afforded N-formylazetidin-2-ones.The influence of pyridine in oxidations by means of NDC is further shown in the conversion of hydroquinones into quinones. Another interesting feature associated with the use of this reagent is the ease of purification of the final products.

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