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3 Monomer Cyclic Monc )mers (Heterocyclics) Initiator system Remarks Re ferences Oxides Ethylene oxide Na, Κ catalysts in (Me 2N) 3PO Na, K, or Cs naphthalenes in THF + + + K , Cs , Na in Me2SO 52 Li naphthalene, Κ naphthalene, Κ bi­ phenyl, Κ anthracene, or di-K an­ thracene in Me2SO or THF Na, K, and Cs naphthalene in THF Na and Κ alcoholates of the monomethyl ether of diethylene glycol in (Me 2N) 3PO /-BuOK in Me 2SO Na naphthalene in THF r-BuOK in Me 2SO BuONa MeOK, MeONa, MeOLi Na alco'holate/alcohol Κ 4-(phenylazo)benzyl alcoholate Cs 3,6-dioxa-l-octanolate in Me 2SO at 50 C wa s Relation between M H V IGNand Mdeact ivated calculated and compared with experimental result Polymerization kinetics + + + Κ and Cs chain growth only via free ion; Na ion pairs also participated in the reaction; chain transfer to solvent No propagation occurred with Li naphthalene; polymers obtained for the other initiators 592 Strong association; living systems Association presence; reaction rate depressed by ΚΒΦ 4 596 597 Polymerization kinetics.

1 •nd Monomers (continued) Initiator system Monomer 2-Isopropenylthiazole Double and Triple ft-BuLi, bulk; MgBr 2, toluene at 0° and 25°C ft-BuLi, bulk or hexane at 25°C BuLi or i-BuONa Remarks Re ferences Soluble polymers 451 Traces of polymer Oligomeric polypeptides 451 452 Low temperature ( —78°C); threo diisotactic configuration Transition polymerization occurred No termination High molecular weight Mixture of isotactic (32%), syndiotactic (13%), and heterotactic (55%) blocks The polymerization rate is slowed down by polymetha+ crylonitrile, water or ΜεΦ 3Ρ Ι~ ; reaction proceeds by a zwitterionic mechanism 453 BuLi in hexane and THF «-Butane formation and nitrile addition are important under these conditions 417 5-BuLi in benzene The nature of the active centers 458 Κ and Na α-methylstyrene oligomers, s-BuLi in THF at -70°C The active centers are able to attach to the cyano groups of some aromatic nitriles and to the carbonyl of benzophenone (added) 459 Et 3P in DMF Termination reaction by water 460 Et 3P Anionic zwitterion-type polymerization 461 N-Methyl-a-methylbeinzeneacrylamide rc-Butyllithium in toluene at 22° and -50°C Optically active polymer 462 2-Methyleneglutaroni trile Li naphthalene ( —35°C) or diphenylmethanelithium (-70°C) in DMF NaCN in DMF at -42 to -32°C Nearly white polymer (yield > 75%) with broad Μ WD and high degree of branching 463 Colorless polymer at low yield 464 Nitroethylene RNH 4-Vinyl- or 4-isopropenylthiazole Maleamide Mesaconamide Maleimides (N-substiltuted) Methacrylamide Methacrylonitrile «-BuLi in toluene and tetrahydrofuran 5-BuONa in polar solvents Lithium in NH 3 Sodium in NH 3 H-BuLi in toluene, — 78°C 40 Et 3P in THF 391 454 455 456 457 465 2-Nitrobutene 1-Nitropropene Phenylacetylene H-Butyllithium in DMSO; lithium in DMF and DMSO; LiAlH4 in tolu­ ene; NaH in DMSO; Na naphtha­ lene in THF; NaCN in DMF and CH2C12 Potassium bicarbonate BuLi in toluene, THF, or DMF MeONa tt-BuLi in heptane/(Me2N)3PO High conversions and low molecular weight polymer at 25°C; low temperatures (~ -78°C) may lead to the formation of high molecular weight material 466 High polymer Soluble amorphous polymer with MW ~ 38,000 Partly insoluble, with some degree of ordering Polymerization kinetics.

Ketones give only 9-17% fractions containing Na ion. -Butane and conjugate addition products observed. 5%) was obtained with Κ in benzene. 3 Monomer Cyclic Monc )mers (Heterocyclics) Initiator system Remarks Re ferences Oxides Ethylene oxide Na, Κ catalysts in (Me 2N) 3PO Na, K, or Cs naphthalenes in THF + + + K , Cs , Na in Me2SO 52 Li naphthalene, Κ naphthalene, Κ bi­ phenyl, Κ anthracene, or di-K an­ thracene in Me2SO or THF Na, K, and Cs naphthalene in THF Na and Κ alcoholates of the monomethyl ether of diethylene glycol in (Me 2N) 3PO /-BuOK in Me 2SO Na naphthalene in THF r-BuOK in Me 2SO BuONa MeOK, MeONa, MeOLi Na alco'holate/alcohol Κ 4-(phenylazo)benzyl alcoholate Cs 3,6-dioxa-l-octanolate in Me 2SO at 50 C wa s Relation between M H V IGNand Mdeact ivated calculated and compared with experimental result Polymerization kinetics + + + Κ and Cs chain growth only via free ion; Na ion pairs also participated in the reaction; chain transfer to solvent No propagation occurred with Li naphthalene; polymers obtained for the other initiators 592 Strong association; living systems Association presence; reaction rate depressed by ΚΒΦ 4 596 597 Polymerization kinetics.

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