Effect of cyclodextrin complexation on photo-fries rearrangement of naphthyl esters

Photolysis of beta-cyclodextrin inclusion complexes of 1- and 2-naphthyl es ters (acetates and benzoates) in aqueous medium, results in rearrangement t o give one isomer of acylnaphthol in excess, whereas the solid state irradi ation of the cyclodextrin complexes yields selectively one isomer. ID addit ion, formation of cleavage product is totally suppressed. This remarkable s electivity is attributed to specific modes of the complexation of the ester s into the beta-CD cavity. (C) 1999 Elsevier Science Ltd. All rights reserv ed.