Oxidation of Alcohols with Nitroxyl Radical Resins under Two-Phase Conditions

Yoshitomo Kashiwagi; Hiroshi Ikezoe; Tetsuya Ono

doi:10.1055/s-2005-922775

LETTER

Oxidation of Alcohols with Nitroxyl Radical Resins under Two-Phase Conditions

Yoshitomo Kashiwagi*^a, Hiroshi Ikezoe^b, Tetsuya Ono^b
^a School of Pharmaceutical Sciences, Ohu University, 31-1 Misumido, Tomita-machi, Koriyama, Fukushima 963-8611, Japan
Fax: +81(24)9329138; e-Mail: y-kashiwagi@pha.ohu-u.ac.jp;
^b Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan

Abstract

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Abstract

The oxidation of alcohols to carbonyl compounds such as aldehydes and ketones was studied using potassium hexacyanoferrate(III) mediated by nitroxyl radical polystyrene resins as catalyst under organic-aqueous two-phase conditions. Primary alcohols are readily oxidized to the corresponding aldehydes in excellent yield with no overoxidation to carboxylic acids. Secondary alcohols are converted to the corresponding ketones with a much lower efficiency. Oxidative cyclization of 1,4- and 1,5-diols to γ- and δ-lactones, respectively, proceeded nicely.

Key words

nitroxyl radical resin - potassium hexacyanoferrate(III) - alcohol - oxidation - two-phase conditions

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References

References and Notes

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