Site-Selective Intramolecular Photocycloaddition of 2-Alkenyl-Substituted 1-Cyanonaphthalenes Depending on Additives, Solvents, and Substituents

Abstract

Irradiation of 2,3-dimethylbut-2-enyl 1-cyano-2-naphthylmethyl ether in the presence of Eu(hfc)₃ in benzene site-selectively afforded the (2π + 2π) intramolecular photocycloadduct at the 1,2-position on the naphthalene ring. On the other hand, allyl 1-cyano-2-naphthylmethyl ether in the presence of Mg(ClO₄)₂ in acetonitrile gave the photocycloadduct at the 3,4-position as a sole product.

Key words

photochemistry - site-selectivity - cycloadditions - intramolecular photoadditions - cycloreversion

References

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Mizuno, K.; Maeda, H.; Sugimoto, A.; Chiyonobu, K.; In Supramolecular Photochemistry; Ramamurthy V., Schanze K. S., Eds.; Marcel Dekker: in press.