Facile Synthesis, Crystal Structure, and Oxidizability of a Novel Benzene Tris-Annelated with Bicyclo[2.2.2]oct-2-ene

Trimerization of 2,3-dibromobicyclo[2.2.2]oct-2-ene by the use of butyllithium followed by subsequent cyclization gives 1,2:3,4:5,6-tris(bicyclo[2.2.2]oct-2-eno)benzene (3), the highly symmetrical structure of which is established by X-ray crystallography. Compound 3 is reversibly oxidized upon cyclic voltammetry at 1.25 V vs Ag/Ag+ in CH3CN.