Detail of "67174-25-8"

Reference

Enantioselective extraction of di-O-benzoyltartrate anion by ion-pair extractant having binaphthyl-unit

Enantioselective extraction of di-O-benzoyltartrate anion by ion-pair extractant having binaphthyl-unit. Ohki, Akira; Miyashita, Ryo; Naka, Kensuke; Maeda, Shigeru (Fac. Eng., Kagoshima Univ., Kagoshima 890, Japan). Bull. 137476-83-6 and 67174-25-8 are also occured in this study. Chem. Soc. Jpn., 64(9), 2714-19 (English) 1991. CODEN: BCSJA8. ISSN: 0009-2673. DOCUMENT TYPE: Journal CA Section: 68 (Phase Equilibriums, Chemical Equilibriums, and Solutions) A lipophilic diphosphonium salt I having binaphtyl-type axial chirality was developed as a novel ion-pair extractant. By use of (R)-I, (-)-di-O-benzoyltartrate ((-)-DBT) was extd. more effectively than (+)-DBT. The enantioselectivity (a = D(-)/D(+); D: distribution ratio) was 1.3-1.4. When monophosphonium-type extractants (where R = H or C8H17) having structures similar to that of I were used, the enantioselectivity was heavily lowered. Equil. studies revealed that the extn. occurs via formation of a 1:1 ion-pair complex between I and DBT at pH 7.5-8.0. The effects of pH, ionic strength, and temp. on the extractability and the enantioselectivity were investigated. The enantioselectivity decreased with lowering pH, and was higher at lower temps. The optical purity of DBT in the aq. phase was gradually enhanced by multistage extn. From an NMR anal. of the I-DBT complex, the resonances of methylene-protons adjacent to phosphonium in the more extractable complexes ((R)-I.(-)-DBT and (S)-I.(+)-DBT) shifted to a higher field compared to those of the less extractable complexes ((R)-I.(+)-DBT and )S)-I.(-)-DBT). .