Enantiomerization of 1 was found to proceed ca. 10 times faster in hexane than in methanol. This has been attributed to the difference in ΔS ‡ found in the respective solvents. The presence of a chiral HPLC stationary phase (Whelk-O1) did not affect the rate of enantiomerization to any significant extent. The previously determined enantiomerization (by inversion of configuration) barrier of 2 using DHPLC (80 kJ mol–1), is thus considered correct, and not biased by the presence of the stationary phase.
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Oxelbark et al. (1999) studied this question.
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