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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 19
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Original Articles

One-Pot Oxidation of Alanine and Its Ethyl Ester with a Mild Oxidant 4′-Methylazobenzene-2-sulfenyl Bromide

, &
Pages 2870-2875 | Received 07 May 2010, Published online: 29 Jun 2011
 

Abstract

One-pot oxidation of alanine and its ethyl ester with a mild oxidant 4′-methylazobenzene-2-sulfenyl bromide is described. Using a nonreactively water-soluble electrophilic species, 4′-methylazobenzene-2-sulfenyl bromide, with L-alanine and its ethyl ester (in 3:1 molar proportions) in aqueous solution at room temperature, the corresponding sulfenimines are prepared. On hydrolysis in acidic medium at room temperature, these sulfenimines give ethanal and pyruvic acid respectively.

ACKNOWLEDGMENTS

We thank the director of NIT, Silchar, for laboratory facilities and the Council of Scientific and Industrial Research, New Delhi, for the award of a junior research fellowship to T. B.

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