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Preparation, resolution and absolute configuration of 2,2′-bipyridine-3,3′-dicarboxylic acid 1,1′-dioxide and its ester

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
6
Issue
6
Identifiers
DOI: 10.1016/0957-4166(95)00160-q

Abstract

Abstract The title racemic acid (±)- 1, prepared by hydrogen peroxide oxidation of 2,2′-bipyridine-3,3′-dicarboxylic acid, was resolved via the brucine salts. The absolute configuration of acid (+)- 1 was determined by X-ray diffraction study of its barium salt using the Bijvoet's anomalous dispersion method. The activation energy ΔG # for interconversion of enantiomers of the dimethyl ester 2 was found to be −106.5 kJ/mol at 50 °C.

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