Synthesis and Characterization of Cyclophenacenes

Deprotonation of the cyclopentadiene in 3 with KO Bu in THF afforded an anion, [K(THF)n][C60Me5(CN)Ph5], which reacted with [PdCl(at-allyl)]2 to give a pal- 

ORTEP drawing of 8 C6H5CI molecules found model, (c) Bottom view of CPK model, 

The structures of the model compounds C40H20 (A) and C60H12 (B) (Chart 2.1) were optimized with quantum mechanical calculations at various levels of theory (semiempirical, Hartree-Fock and hybrid density functional methods) and were found to reproduce the experimental data very well (within ca. 1.5%, Table 2.1). The optimized structures and experimental structures of A and B also match well with the structure obtained from an estimation of the Pauli bond order [34] assuming equal contributions of all 125 canonical resonance structures. 

---