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Molecules 2017, 22(3), 491; doi:10.3390/molecules22030491

[2 + 2] Photodimerization of Naphthylvinylpyridines through Cation-π Interactions in Acidic Solution

Department of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan
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Author to whom correspondence should be addressed.
Academic Editor: Shunichi Fukuzumi
Received: 21 February 2017 / Revised: 8 March 2017 / Accepted: 15 March 2017 / Published: 20 March 2017
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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Abstract

Irradiation of (E)-4-(2-(2-naphthyl)vinyl)pyridine (1a) and (E)-4-(2-(1-naphthyl)vinyl)pyridine (1b) with a 250 W high-pressure mercury lamp in acidic solution afforded synHT dimers in high stereoselectivities. Similar results were obtained by visible light irradiation. On the other hand, when the reactions were carried out under neutral conditions, the stereoselectivities were very low, and the yields were decreased by visible light irradiation. Comparison of the UV-vis spectra between the acidic and the neutral conditions elucidated that the red shift was observed in acidic solutions. These results show that HCl plays essential roles not only in the preorientation of substrates through cation-π interactions, but also in the changes in the absorption properties of substrates that enable visible light reactions. View Full-Text
Keywords: cation-π interaction; [2 + 2] photodimerization; cyclobutane derivative; naphthylvinylpyridine; stereoselective reaction cation-π interaction; [2 + 2] photodimerization; cyclobutane derivative; naphthylvinylpyridine; stereoselective reaction
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Yamada, S.; Nojiri, Y. [2 + 2] Photodimerization of Naphthylvinylpyridines through Cation-π Interactions in Acidic Solution. Molecules 2017, 22, 491.

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