Chiral and meso-bis([2.2]paracyclophan-4-yl)methane and meso-bis([2.2]paracyclophan-4-yl) sulfide

The [2.2]paracyclophane groups of the title compounds, chiral and meso-bis( tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaen-5-yl)methane (the for mer as a racemate), C33H32, and meso-bis(tricyclo[8.2.2.2(4,7)]hexadeca-4,6 ,10,12,13,15-hexaen-5-yl) sulfide, C32H30S, show the characteristic structu ral features of the parent compound [2.2]paracyclophane and the related com pound dimethylbis([2.2]paracyclophan-4-yl)-silane, C34H36Si: the aromatic r ings are puckered, resulting in a boat conformation. The planes of the four coplanar C atoms are slightly twisted with respect to each ether. The Csp( 3) - Csp(3) bond lengths of the ethylene bridges are elongated by the elect ronic and steric effects of the skeleton.