Oxone-Mediated Oxidative Cleavage of β-Keto Esters and 1, 3-Diketones to α-Keto Esters and 1, 2-Diketones in Aqueous Medium

A Stergiou, A Bariotaki, D Kalaitzakis…

Index: Stergiou, Anastasios; Bariotaki, Anna; Kalaitzakis, Dimitris; Smonou, Ioulia Journal of Organic Chemistry, 2013 , vol. 78, # 14 p. 7268 - 7273

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Citation Number: 19

Abstract

A versatile and highly efficient method for the direct synthesis of α-keto esters and 1, 2- diketones has been developed. This approach utilizes the oxidative cleavage of a variety of β-keto esters and 1, 3-diketones mediated by an Oxone/aluminum trichloride system. The simple one-step oxidation reaction proceeded selectively in aqueous media to afford products in high yields, short reaction times, and environmentally benign conditions.

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Efficient preparation of polyfunctional. alpha.-diketones fr...

[Conrow, Raymond; Portoghese, Philip S. Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 938 - 940]

A novel monoalkylation of symmetrical α-diones

[Gopal, Damodaragounder; Nadkarni, Durgesh V.; Sayre, Lawrence M. Tetrahedron Letters, 1998 , vol. 39, # 14 p. 1877 - 1880]