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

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