Selectivity variation in hydrolysis of phenyl acetates by simple modifications of β-cyclodextrin.

By reaction of β-cyclodextrin 6-monotosylate with alkyl mercaptans, 6-deoxy-6-alkylthio-β-cyclodextrins, $\text{2}$, $\text{3}$, and $\text{4}$, were prepared. Studies of the hydrolyses of $\text{m}$- and $\text{p}$-substituted phenyl acetates showed that the well-known meta-selectivity effect occurred with $\text{2}$, while none was observed with $\text{4}$. This variation in selectivity was due to a change in the catalytic rate constant caused by the substituent on β-cyclodextrin.