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Enhancement of Reactivity of the Ester Carbonyl Group By Interchromophoric Links in Photochemical Cycloadditions. Intermediacy and Roles of Plural Intramolecular Exciplexes

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9-Phenanthrenecarboxylic esters as well as naphthalenecarboxylic esters linked with p-methoxystyrene derivatives exert an intramolecular competitive or exclusive oxetane formation through carbonyl addition, although the carbonyl addition is not observed in the corresponding intermolecular systems. The reaction proceeds from the excited singlet state involving plural intramolecular exciplexes. The new aspect of carbonyl addition, i.e., the enhancement of reactivity of the ester carbonyl group by interchromophoric links, is discussed on the basis of photochemical and photophysical observations as well as MO calculations.

Affiliations: 1: Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki 305, Japan; 2: Department of Chemistry, Faculty of Science, Yamagata University, Koshirakawa, Yamagata 990, Japan


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