Abstract
AbstractThe acid‐catalysed solvolysis of (R)‐1‐phenyl‐1‐methoxyethane was studied in mixtures of dilute aqueous perchloric acid and acetonitrile at 50°C. The rate of loss of optical activity (kα) was found to be the same as the rate of solvolysis (ksolv) at both low and high water contents of the solvent. These results are not in accord with literature data on racemization and oxygen exchange of 1‐phenylethanol in water, which has been discussed in terms of interconversion of chiral ion–dipole pair intermediates. The mechanistic implications of the results are discussed.
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