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α/β-Selectivity in Hydrolyses of α- or β- Naphthyl Acetates in the Presence of Cycloamyloses.

✍ Scribed by Kahee Fujita; Seiji Ejima; Taiji Imoto

Book ID
104242274
Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
204 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

Cyclohexaamylose hydrolyzed u-naphthyl acetates more rapidly than the corresponding 8-isomers, a phenomenon termed "e-selectivity", while cyclooctaamylose showed "8-selectivity" and the selectivity of cycloheptaamylose fell between those of cyclohexa-and cycloocta-amyloses.

On the hydrolyses of substituted phenyl acetates by cyclohexaamylose or cycloheptaamylose, meta-substituted phenyl esters were more rapidly hydrolyzed 1 than the corresponding para-isomers, a phenomenon termed "meta-selectivity" .

This selectivity is attributed to the structure of the inclusion complex'. Therefore, in the case of the hydrolysis of the substrate which has more than two structures of productive inclusion-complexing, the selectivity is expected to depend on the cavity size of the cycloamylose.

In this paper, we wish to demonstrate "a/8-selectivity" in hydrolyses of o-or 8-naphthyl acetates (la-c and 2c,d) by cyclohexa-, cyclohepta-, and

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