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Optisch aktive aromatische Spirane, 7. Mitt. Circulardichroismus optisch aktiver 5,5′-disubstituierter 2,2′-Spirobiindane

Optically active, aromatic spiranes, VII: Circular dichroism of optically active 5,5′-disubstituted 2,2′-spirobiindanes

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Abstract

Dipole-dipole coupling of the indane fragments in 5,5′-disubstituted 2,2′-spirobiindanes is predominantly responsible for the origin of optical activity in the1La-electronic transition only if both ligands exhibit strong interaction with the aromatic nuclei. This mechanism does not contribute essentially to the1Lb-Cotton effect.

The band-splittings of the couplet as well as the rotational strengths of the transitions ofA andB symmetry-type in the1La-Cotton effect are in accordance with a rough calculatory estimation.

The absolute configuration thus determined agrees with the chirality recently deduced by chemical methods.

The rotational strengths of the1W-Cotton effect of the carbonyl derivatives4, 5, 12, 13, and15 located at appr. 320 nm are remarkably low. This can be explained on the basis of conformational considerations.

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6. Mitt.:H. Neudeck undK. Schlögl, Chem. Ber.110. 2624 (1977).

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Langer, E., Lehner, H., Neudeck, H. et al. Optisch aktive aromatische Spirane, 7. Mitt. Circulardichroismus optisch aktiver 5,5′-disubstituierter 2,2′-Spirobiindane. Monatshefte für Chemie 109, 987–999 (1978). https://doi.org/10.1007/BF00907320

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