Cyclic electron delocalization in hydrocarbon cages (pagodanes, isopagodanes, (bisseco-/seco-)-(dodecahedradienes)

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Abstract

In the polycyclic, rigid [l.l.l.l]/[2.2.1.1] (iso)pagodanes and in the related (bisseco/seco)dodecahedradienes the geometrical and energetical situation for the 4c/3e radical cations and 4c/2e dications produced by loss of one or two electrons from the central cyclobutane/homodiene cores is gradually modified. By spectroscopic (UV, PE, ESR, NMR), cyclovoltammetric, and theoretical investigations the structural prerequisites and the degree of homoconjugational (through-cage) electron delocalization (σ-homoaromaticity) are explored. © 1995 IUPAC

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Prinzbach, H., Gescheidt, G., Martin, H. D., Herges, R., Surya Prakash, G. K., & Olah, G. A. (1995). Cyclic electron delocalization in hydrocarbon cages (pagodanes, isopagodanes, (bisseco-/seco-)-(dodecahedradienes). Pure and Applied Chemistry, 67(5), 673–682. https://doi.org/10.1351/pac199567050673

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