Optical Activity of Bis-1,1′-spiroindanes. I. Optical Resolution and Absolute Configuration

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概要

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• The resolutions of 6,6′-dihydroxy-3,3,5,3′,3′,5′-hexamethyl-bis-1,1′-spiroindane (IIIa), 3,3,3′,3′-tetramediyl-bis-1,1′-spiroindane-6,6′-dicarboxylic acid (IIIc), and 5,5′-dihydroxy-bis-1,1′-spiroindane (VIII) are reported. The circular dichroism and absorption spectra of these optically active compounds and their derivatives were measured. The spectra were analysed by means of a coupled oscillator model. The relative frequencies and signs of the rotational strengths associated with the <I>p</I>-band transition calculated for the (S)-configuration of 6,6′-disubstituted-bis-1,1′-spiroindanes agree with the positions and signs of the CD bands observed for the compounds derived from (−)-IIIc, establishing the absolute configuration of this series. The result was confirmed by the X-ray diffraction study of (−)-7,7′-dibromo-derivatives prepared from (+)-IIIa. It was found that these spiro compounds having the (S)-configuration showed a negative CD band in the longest wavelength region, except for the case in which the effect of the charge transfer between two aromatic chromophores overwhelmed that of the dipole-dipole interaction.

• 公益社団法人 日本化学会の論文

著者

• Hagishita Sanji

  Shionogi Research Laboratories Shionogi And Co. Itd.

• Hayashi Masanori

  Department Of Aeronautical Engineering Kyushu University

• Nakagawa Masazumi

  Department of Chemistry Faculty of Science Osaka University

• Kuriyama Kaoru

  Shionogi Research Laboratories, Shionogi & Co. Ltd.

• Nakano Yasuko

  Department of Chemistry, Faculty of Science, Hokkaido University

• Nakano Yasuko

  Department of Chemistry, Faculty of Science, Osaka University

• Shingu Keiji

  Department of Chemistry, Faculty of Science, Osaka University

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