Addition of sec-butyllithium to m-diisopropenylbenzene

The reaction of equivalent quantities of sec-butyllithium with m-diisopropenylbenzene in cyclohexane and benzene solution in the presence and absence of catalytic amounts of triethylamine, does not yield the diadduct quantitatively. Oligomer formation occurs to varying extents depending on the reaction conditions, and, contrary to claims in the literature, this may not be a good route to a difunctional initiator for anionic polymerization.