Issue 9, 2011
From the journal:

Photochemical & Photobiological Sciences

Hydrogen-bonding directed, regioselective photocycloaddition reactions of cyanonaphthalenes with furanmethanols†‡

Hajime Maeda,a   Kazuhiko Chiyonobub  and  Kazuhiko Mizuno*b  

* Corresponding authors

a Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa, Japan
E-mail: maeda-h@t.kanazawa-u.ac.jp
Fax: +81-76-234-4800
Tel: +81-76-264-6290

b Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, Japan
E-mail: mizuno@chem.osakafu-u.ac.jp
Fax: +81-72-254-9289
Tel: +81-72-254-9289

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 1H 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.

Graphical abstract: Hydrogen-bonding directed, regioselective photocycloaddition reactions of cyanonaphthalenes with furanmethanols

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Article information

DOI
https://doi.org/10.1039/C1PP05060E
Article type
Paper
Submitted
05 Feb 2011
Accepted
18 Mar 2011
First published
21 Apr 2011

Photochem. Photobiol. Sci., 2011,10, 1445-1449

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Hydrogen-bonding directed, regioselective photocycloaddition reactions of cyanonaphthalenes with furanmethanols

H. Maeda, K. Chiyonobu and K. Mizuno, Photochem. Photobiol. Sci., 2011, 10, 1445 DOI: 10.1039/C1PP05060E

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