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Issue 6, 1989
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The syn conformers of several 2,11-dithia[3.3](1,4)naphthalenometacyclophanes: novel preference for a conformation with parallel benzenoid rings from direct confrontation of two different modes of non-bonding interaction

Yee-Hing Lai 

Abstract

2,11-Dithia[3.3](1,4)naphtha lenometacyclophane and its 9-bromo- and 9-fluoro-derivative have been synthesized. 1H and 19F n.m.r. studies have indicated that all three dithiacyclophanes prefer the syn-conformation with near-parallel stacking of aromatic rings. This conformational preference is supported by results from MMP2 calculations. The angle of tilting of the meta-bridged ring is dependent on the 9-substituent. Variable-temperature n.m.r. studies have unexpectedly shown neither a flipping of the meta-bridged ring nor a wobbling of the C–S–C bridges. Possible conformational behaviour is the continuous tilting process of the meta-bridged ring in the rigid syn-. conformation. A solvent effect on the chemical shifts of both the reference protons and the fluorine has been observed.

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Article type: Paper
DOI: 10.1039/P29890000643
Citation: J. Chem. Soc., Perkin Trans. 2, 1989,0, 643-648
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    The syn conformers of several 2,11-dithia[3.3](1,4)naphthalenometacyclophanes: novel preference for a conformation with parallel benzenoid rings from direct confrontation of two different modes of non-bonding interaction

    Y. Lai, J. Chem. Soc., Perkin Trans. 2, 1989, 0, 643
    DOI: 10.1039/P29890000643

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