Abstract
AbstractThe enantiomeric separation of aryl trifluoromethyl and difluoromethyl sulfoxides was realized via chiral chromatography. The configurational stability of each set of enantiomers was then studied by thermal enantiomerization. The ΔG≠ values obtained cover a range of 38.2–41.0 kcal mol−1 at 214 °C, thus demonstrating their optical stability at room temperature. However, a shorter half‐life time has been observed for difluoromethyl sulfoxides. Furthermore, the acidities of six aryl difluoromethyl sulfoxides were determined in DMSO by an overlapping indicator method using UV‐visible spectrophotometric titrations. The pKa values fall in range of 20.3–22.5 and differ by about 10 log units compared to non‐fluorinated analogues.
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