Structural Effects on Photochemical Cycloaddition of Phenanthrene- and Naphthalenecarboxylic Esters. Enhancement of Reactivity of an Ester Carbonyl Group by Interchromophoric Links

Article abstract of DOI:10.1246/bcsj.66.224

On irradiation in benzene, (E)-5-(p-methoxyphenyl)-4-pentenyl 3-, 9-phenanthrenecarboxylate, 1-, and 2-naphthalenecarboxylate gave novel olefinic aldehydes presumably derived from oxetane presumably derived from oxetane precursors, the intramolecular carbonyl adducts.Intermolecular carbonyl addition was not detected between the corresponding ester and olefinic chromophores.Enhancement of reactivity of the ester carbonyl group in the linked systems is discussed on the basis of experimental and theoretical studies.