Methods are reported for the attachment of -nucleophiles to the primary and secondary sides of the cyclodextrin cavity. Six new materials have been prepared in which /3CD has been modified by hydrazine, hydroxylamine, oxime, and hydroperoxide functionalities. Transacylating studies with p-NPA have demonstrated that the primary-side hydroxylamine shows the highest reactivity with a 1900-fold increase in rate over /3CD at pH 6.5. Other -nucleophiles show less remarkable rate increases in this system but, in some cases, demonstrate hydrogenbonding to the cyclodextrin rim and inhibition kinetics.

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