Synthesis 2001(8): 1197-1202
DOI: 10.1055/s-2001-15068
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Yasuharu Yoshimi, Shin-ichi Konishi, Hajime Maeda, Kazuhiko Mizuno*
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Sakai, Osaka 599-8531, Japan
Fax: +81(722)549289; e-Mail: mizuno@chem.osakafu-u.ac.jp;
Further Information

Publication History

Received 5 March 2001
Publication Date:
24 September 2004 (online)

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.

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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.