Details are reported of the preparation and X-ray structural characterisation of the new compounds (PhCbo)2X, where PhCbo = 2-Ph-1,2-C2B10H10 and X = S (1) or SO (3), prepared from PhCboLi and SCl2 or SOCl2 respectively, as well as the known compound with X = S2 (2). Hydrogen in the presence of palladium/carbon reduced (3) to (1). Features of their structures (exo C–S and cage C–C distances and substituent orientations) are consistent with significant exo Sdouble bond; length as m-dashC dative π-bonding from their sulfur atoms to the cage hypercarbon atoms and weak exo π-bonding from the phenyl groups. Attempts to prepare systems (CboY)2, in which two ortho-carboran-di-yl residues Cbo are linked through two bridging units Y (S, SO) are also reported, as are their calculated structures.