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ChemInform Abstract: Synthesis of 2,4-Diketoacids and Their Aqueous Solution Structures.

✍ Scribed by Lothar Brecker; Mateja Pogorevc; Herfried Griengl; Walter Steiner; Thomas Kappe; Douglas W. Ribbons

Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthesis of 2,4-Diketoacids and Their Aqueous Solution Structures.

-The synthesis of 2,4-diketoacids (IV) and (VII) is achieved by base-mediated condensation of oxalate (I) with methyl ketones (II) and (V) followed by ester hydrolysis. The diketoacids are shown to exist as 2-enols in CHCl 3 solution. In contrast, in aqueous solutions alkyl-and alkenyl-substituted diketoacids exist as a tautomeric mixture of diketo, ketoenol and ketohydrate forms. Additionally, dimers can occur as a product of self-aldol condensation. Aryl-substituted diketoacids form a Ο€-delocalized enolate system in aqueous solutions. Kinetics of the complexation behavior of diketoacids with various metal ions are studied.

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