Abstract
The optical resolution of FClBrCCO2H (FCBAA), an intermediate to fluorochlorobromoacetaldehyde, was carried out by fractional crystallization of its strychnine salt, and 8 samples of optically enriched FCBAA were prepared. The optical purities of the FCBAA samples ranged from 67% (+) to 35% (−) based on 19F NMR studies on their (−)-borneol esters. 1H and 13C NMR spectra of the borneol ester were also investigated in detail using two-dimensional NMR technique. The optical rotations of the fluorochlorobromomethane samples, which were converted from the strychnine salt of FCBAA by thermal decarboxylation, were plotted against the enantiomer excesses of the parent FCBAA, and a good linear relation was obtained.
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Hatada, K., Ute, K., Nakano, T. et al. Haloaldehyde Polymers XXXV. 1H, 19F, and 13C NMR Spectra and Stereochemistry of Bornyl Esters of Fluorochlorobromoacetic Acid. Polym J 21, 171–177 (1989). https://doi.org/10.1295/polymj.21.171
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DOI: https://doi.org/10.1295/polymj.21.171
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