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

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.

Keywords:

• Alanine
• aqueous medium
• oxidation
• sulfenimine

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.