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Issue 0, 1971
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Annulenes. Part XII. The dianion of [12]annulene


[12]Annulene is very unstable and can be reduced by alkali metals at –80° to the corresponding dianion. An n.m.r. study of this species clearly indicates that (i) it has the same perimeter configuration as the parent [12]-21-annulene, (ii) it presents a diamagnetic ring current (14 π-electrons, τ 14·60 for the three inner protons), it is thermally much more stable than the parent [12]-21-annulene, and it does not undergo any dynamical process such as the very fast conformational mobility observed in [12]-21-annulene itself.

All these observations point to an appreciable resonance energy associated with the 14 π-electrons, despite the non-planarity of the ring.

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Article type: Paper
DOI: 10.1039/J29710000904
Citation: J. Chem. Soc. B, 1971,0, 904-907

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    Annulenes. Part XII. The dianion of [12]annulene

    J. F. M. Oth and G. Schröder, J. Chem. Soc. B, 1971, 0, 904
    DOI: 10.1039/J29710000904

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