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- W1974064687 abstract "The photocyclization of 2-styrylbenzo[c]phenanthrene (1) in n-butylamine yields a mixture of hexahelicene (3) and two dihydrohexahelicenes (5 and 6). Both dihydrohexahelicenes could be isolated from the irradiation mixture as pure compounds by chromatography on a silica gel coated with R( - )-TAPA, a chiral stationary phase developed for the resolution of the enantiomers of hexahelicene (3). The NMR spectra of 5,6-dihydrohexahelicene (5) and 7,8-dihydrohexahelicene (6) exhibit remarkable differences in the aromatic region. These differences are attributed to the location of the alicyclic ring in the hexahelicene skeleton. The X-ray structure analyses of the dihydrohexahelicenes 5 and 6 demonstrate that, in the crystalline state, both isomers occur in only one of two possible conformations. The NMR spectra of the two compounds lead to the conclusion that, in solution, the same conformation as in the solid state is highly preferred, although the existence of the second conformation cannot be completely excluded. Structural analyses by forcefield calculations corroborate this conclusion." @default.
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- W1974064687 date "2010-09-02" @default.
- W1974064687 modified "2023-09-25" @default.
- W1974064687 title "Syntheses, conformational analyses, X-ray analyses and force-field-calculations of 7,8-dihydrohexahelicene and 5,6-dihydrohexahelicene" @default.
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- W1974064687 doi "https://doi.org/10.1002/recl.19881071002" @default.
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