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Dianion and Tetraanion of [24] Paracyclophanetetraene—New Unusual Perimeter Systems


  • This work was supported by the Deutsche Forschungsgemeinschaft. Dr. W. Huber thanks the Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung for a grant.


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The existence of peripheral ring currents in the dianion and the tetraanion of (1) is manifested in the NMR spectra. In the case of (1), the dianion, and the tetraanion, H-3 (outer) absorbs at δ = 7.37, 9.26, and 4.48, respectively, and H-4 (inner) at 7.37, −7.07 (!), and 12.76, respectively. From the viewpoint of bonding theory, it is particularly surprising that perimeter conjugation extends beyond the benzene units.

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