Issue 11, 2003
From the journal:

New Journal of Chemistry

Oxidation of alcohols with nitroxyl radical under polymer-supported two-phase conditions

Yoshitomo Kashiwagi,*a   Shinya Chibaa  and  Jun-ichi Anzaia  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, Sendai, Japan
E-mail: kashi@mail.pharm.tohoku.ac.jp
Fax: +81-22-217-6840
Tel: +81-22-217-6842

Abstract

The oxidation of alcohols to carbonyl compounds was studied using potassium hexacyanoferrate(III) mediated by nitroxyl radical as the catalyst under polymer-supported organic–aqueous two-phase conditions. Primary alcohols are readily oxidized to the corresponding aldehydes in excellent yield with no over-oxidation to carboxylic acids. Secondary alcohols are converted to the corresponding ketones with a much lower efficiency. The oxidation reactions of primary alcohols in the presence of secondary alcohols is strongly favored. Primary-secondary diols are selectively transformed into hydroxy aldehydes with small amounts of ketoaldehydes, the amount of isomeric keto alcohols remaining is less than 1%.

Graphical abstract: Oxidation of alcohols with nitroxyl radical under polymer-supported two-phase conditions

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Article information

DOI
https://doi.org/10.1039/B307190C
Article type
Letter
Submitted
24 Jun 2003
Accepted
12 Aug 2003
First published
19 Sep 2003

New J. Chem., 2003,27, 1545-1549

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Oxidation of alcohols with nitroxyl radical under polymer-supported two-phase conditions

Y. Kashiwagi, S. Chiba and J. Anzai, New J. Chem., 2003, 27, 1545 DOI: 10.1039/B307190C

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