Cyclodextrin-accelerated cleavage of phenyl esters: is it the 2-hydroxy or the 3-hydroxy that promotes the acyl transfer?

Abstract

Both 2- and 3-monothiocyclodextrins have been synthesized and used in probing the mechanism of cyclodextrin-mediated cleavage of phenyl esters, showing that the 3-thiols are much more effective than the 2-thiols in promoting the acyl transfer.

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