Tetrahedron letters

Cyclodextrin-mediated regioselective photo-Fries reaction of 1-naphthyl phenyl acylates

S Koodanjeri, AR Pradhan, LS Kaanumalle…

Index: Koodanjeri, Smriti; Pradhan, Ajit R.; Kaanumalle, Lakshmi S.; Ramamurthy Tetrahedron Letters, 2003 , vol. 44, # 15 p. 3207 - 3210

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Citation Number: 14

Abstract

1-Naphthyl phenyl acylates upon irradiation in solution yield eight products via β-cleavage process. However, excitation of these molecules as included in γ-cyclodextrin results in a single product (> 95%). This medium dependent product selectivity is attributed to conformational and translational restrictions enforced on the reactant as well as intermediates by the cyclodextrin cavity.