Action du sec‐butyllithium sur le bis(isopropényl‐4 phényl)‐1,1 phényl‐1 tridécane en milieu solvant non‐polaire

The reaction of sec‐butyllithium with 1,1‐bis(4‐isopropenylphenyl)‐1‐phenyltridecane (3) yields carbanionic species which are soluble in a non‐polar solvent. The long hydrocarbon “tail” of the molecule and the tendency of the organolithium compounds to associate may be the reason for the high solubility, possibly due to micel‐formation. In the absence of any sidereaction, the addition reaction should lead to a difunctional organolithium compound. However, UV spectrometric measurements and characterization by size exclusion chromatography of the species obtained after protonation of the anionic sites, show that oligomerization accompanies the di‐addition reaction with formation of principally dimeric and a small fraction of trimeric molecules. This implies the existence of di‐, tri‐ and tetracarbanionic species in the “living” reaction media.