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Reduction of the formally antiaromatic compound 1,3,5,7-tetra-tert-butyl-s-indacene to the dianion 1 is achieved with lithium or potassium. Both salts were characterized by NMR spectroscopy and X-ray crystallography, which revealed that the polycyclic hydrocarbon framework exhibits a delocalized π-electron system, as does the neutral compound. The results of density functional theory calculations are in agreement with the experimental findings.
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Cary et al. (1997) studied this question.
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