Tetrahedron: Asymmetry

Experimental and theoretical investigations of absolute stereochemistry and chiroptical properties of enantiopure 2, 2′-substituted 9, 9′-bianthryls

S Toyota, T Shimasaki, N Tanifuji, K Wakamatsu

Index: Toyota, Shinji; Shimasaki, Toshiaki; Tanifuji, Naoki; Wakamatsu, Kan Tetrahedron Asymmetry, 2003 , vol. 14, # 12 p. 1623 - 1629

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Citation Number: 16

Abstract

The absolute stereochemistry of axially chiral 2, 2′-X2-9, 9′-bianthryls (X= COOH, COOMe, and Cl) was determined by X-ray analysis of the (+)-quinidine salt of the diacid to be (M)-(−) or (P)-(+). The M isomers of these compounds showed specific rotations of− 115,− 123, and− 32, respectively, in acetone. The circular dichroism (CD) as well as UV spectra of the two M isomers (X= COOMe and Cl) were investigated with the aid of theoretical ...