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

HS Banu, K Pitchumani, C Srinivasan

Index: Banu, Habeeb Shayira; Pitchumani, Kasi; Srinivasan, Chockalingam Tetrahedron, 1999 , vol. 55, # 31 p. 9601 - 9610

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Citation Number: 17

Abstract

Photolysis of β-cyclodextrin inclusion complexes of/kl-and 2-naphthyl esters (acetates and benzoates) in aqueous medium, results in rearrangement to give one isomer of acylnaphthol in excess, whereas the solid state irradiation of the cyclodextrin complexes yields selectively one isomer. In addition, formation of cleavage product is totally suppressed. This remarkable selectivity is attributed to specific modes of the complexation of the esters into the β-CD ...