Novel twin corannulene: synthesis and crystal structure determination of a dicorannulenobarrelene dicarboxylate

Org Lett. 2003 Jul 24;5(15):2595-7. doi: 10.1021/ol034692i.

Abstract

[reaction: see text] The dicorannulenobarrelene 1 was synthesized with the final step achieved by a nickel-mediated fourfold intramolecular coupling of dibromomethyl with bromomethyl groups. Low-temperature (1)H NMR spectra of 1 show a presence of three conformers with approximate populations of 0.82:0.13:0.05, in good agreement with theoretical predictions. In the crystal, 1 incorporates two CCl(4) molecules and adopts the bis-exo conformation.