Add time:07/28/2019         Source:sciencedirect.com

The product of two-electron reduction of 3-thiohydroxy 2-oxo propanoic 1 acid is either β-mercaptolactate or pyruvate when the CS cleaved. The first pathway predominates in acidic media, the second in slightly basic media. Comparison of the polarographic and UV and NMR spectrometric behaviour of 1 with that of thioether C2H5SCH2COCO2H 2 indicates that, in the second dissociation step for 1 (pk2 = 9.6), kinetically controlled formation of the thiolate anion occurs which is slowly converted into an ambident carbanion. A ketol dimeric product was isolated as sodium salt and its structure established by 13C NMR study. The ability to form ambient carbanion in slightly basic medium is of importance in essential biological processes.

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