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Synthesis and Properties of Butterfly-Shaped Expanded Naphthofuran Derivatives

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† Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Shimogamo, Sakyo-ku Kyoto 606-8522, Japan
‡ Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011, Japan
*E-mail: [email protected]
Cite this: J. Org. Chem. 2014, 79, 6, 2625–2631
Publication Date (Web):February 24, 2014
https://doi.org/10.1021/jo500085a
Copyright © 2014 American Chemical Society
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Abstract

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The construction of dinaphtho[2,1-b;2′,3′-d]furan-6-ol was developed via a dehydration reaction involving two molecules of 2,3-dihydroxynaphthalene in the presence of a strong acid. Starting from the dinaphthofuran, a variety of butterfly shaped derivatives were synthesized. The optical properties of these compounds were investigated with special attention to the dihedral angle formed by adjacent dinaphthofuran rings and/or the sizes of the fused aromatic rings.

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The coordinates of naphthofuran derivatives (dihedral angle fixed compound 6, optimized structures of compound 6, dealkylated compound 11, and dealkylated compound 12 in the absence or presence of THF) by DFT calculation, 1H and 13C NMR spectra for all new compounds, and CIF of compound 3 (CCDC 986435). This material is available free of charge via the Internet at http://pubs.acs.org.

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  27. Kentaro Nakanishi, Takahiro Sasamori, Kouji Kuramochi, Norihiro Tokitoh, Takeo Kawabata, Kazunori Tsubaki. ChemInform Abstract: Synthesis and Properties of Butterfly-Shaped Expanded Naphthofuran Derivatives.. ChemInform 2014, 45 (35) , no-no. https://doi.org/10.1002/chin.201435123
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