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Updated: Jun 2, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Hydrogen-bonding directed, regioselective photocycloaddition reactions of cyanonaphthalenes with furanmethanols
Hajime Maeda1, Kazuhiko Chiyonobu, Kazuhiko Mizuno
1Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Ishikawa, Japan. maeda-h@t.kanazawa-u.ac.jp
Abstract:
1-Cyanonaphthalene and 2-cyanonaphthalene react with 2-furanmethanol and 3-furanmethanol, respectively, under photoirradiation conditions to give [4 + 4] photocycloadducts and caged compounds with high degrees of regioselectivity. Analysis of data obtained from variable temperature (1)H NMR and fluorescence quenching experiments indicates that hydrogen bonding between cyano and hydroxy groups in the excited states of the corresponding naphthalene and furanmethanol substrates is the source of the observed regioselectivities.
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