Mingyue Liu, Bao Zhang, Mingliang Chen, Shuo Wang, Xiangge Zhou, Haifeng Xiang
Despite a high rotational barrier from ortho-methyl groups, sym-tetraacetylethane-a distally axially chiral molecule with intramolecular hydrogen bonds-cannot be resolved by chiral HPLC. DFT reveals an unusual racemization pathway via hydrogen-bond-assisted intramolecular proton migration (barrier 1.33-3.00 kcal mol-1) that interconverts enantiomers without axial rotation or bond breaking, supported by NMR and UV-vis spectra.