Relative reactivity of cationic monomers: Isobutylene, styrene and ring substituted styrenes

POLY 101

Nagesh Kolishetti, Nagesh_Kolishetti@uml.edu and Rudolf Faust, Rudolf_Faust@uml.edu. Department of Chemistry, University of Massachusetts Lowell, One University Ave., Lowell, MA 01854
The addition reaction of isobutylene (IB), styrene (St) and p-methylstyrene (pMeSt) to living poly(p-methoxystyrene) (PpMeOSt+) obtained using 1-chloro-1-(p-methoxyphenyl)ethane (pMeOStCl)/SnBr4 initiating system in CH2Cl2 from –40 to –0 °C in the presence of 2,6-di-tert-butylpyridine (DTBP) as proton trap was studied. Quantitative crossover to IB, St and pMeSt was observed and changing the temperature and concentrations could control the number of monomer units incorporated per chain before irreversible ion collapse. Competition experiments were used to determine the reactivity ratios, kp/k12, where kp is the propagation rate constant of pMeOSt. Based on the reactivity ratios calculated from the limiting conversions and limiting molecular weights, at –40 °C pMeOSt is 38, 251, 322 and 634 times more reactive than pMeSt, IB, St and p-chlorostyrene respectively. These values are in good agreement with the nucleophilicity parameters reported by Mayr.