Anionic Polymerization: Principles and Practice by Maurice Morton

By Maurice Morton

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Fluorenylalkali metals in ether or (Me 2N) 3PO Cumylcesium or a-methylstyrylcesium in THF at - 75°C /-BuOK in Me2SO 27 Li biphenyl in dimethoxyethane Na l,3-diphenyl-l,2,3-propanetrionein 1,2-dimethoxyethane Benzyl sodium in 1,2-dimethoxyethane or THF Na naphthalene, Na anthracene, Na triphenylmethane, Na or Li benzophenone, or the Michler ketone Ν a salt 9-Fluorenyllithium in 5-10% THF in toluene (- 60°C) Li biphenyl in aromatic hydrocarbons Na or Κ in Me 3N Oligoester acrylate Ν a naphthalene Phenyl acrylate Phenyl methacrylate ß-Styryl acrylate 2,2,6,6-Tetramethyl-4-piperidinol1-oxyl methacrylate p-Tolyl methacrylate BuLi in toluene at — 50°C «-BuLi in toluene and THF Optically pure 2-methylbutyllithium 0MgBr in toluene or chloroform at 0°C Trityl methacrylate BuLi, Na naphthalene, LiAlH 4 in tol­ uene and THF «-BuLi, (0MgBr) Syndiotactic polymer 238 Reaction proceeds without any detectable side reacti on; narrow Μ WD Polymerization rapid and complete at 25°C; initial tion believed to occur via the MeSOCH2 ion with the monomer Syndiotactic polymer; bimodal Μ WD Does not induce anionic polymerization; effective pui ifying agent in the removal of H20, 02, etc.

3 Monomer Propylene oxide (continued) Heterocyclic Monomers (continued) Zn salts of xanthates, dithiocarbamates and thiocarboxylates i-BuN(EtZn) 2 + H 20 (trace) (bulk) f-Butyl oxirane /-BuOK or dimsylsodium at 30-60 C in Me2SO and Me2SOTHF mixtures Zn salts of xanthates, dithiocar­ bamates, and thiocarboxylate ZnEt 2-H 20 2,3-Dideuteromethyloxirane Trifluoromethyloxirane ZnEt 2-H 20, 65 C, bulk; ί-BuOK at 96 C /-BuOK in bulk or Zn(OCH 3) 2 in benzene (RO) 2Zn in benzene at 3 5 C KOH Epichlorohydrin Monosodium salt of hexafluoropentanediol NaOH 1,2-Butylene oxide 54 Optically active 2-methyl butylglycidyl ether Optically active methyl[ glyciidyl ether Isoamyl glycidyl ether Styrene oxide Remarks Initiator system KOH in hexane KOH Et 2Zn/H 20 or KOH MeOK at 80 C Potassium aromatic nitriles or ketones in THF (65-80 C) Re ferences High polymers 618 Isotactic polymer, addition of water enhances rate and also yield of isotactic Reaction mechanism 619 High polymers 618 Structural studies of the isotactic polymer by X-ray diffraction method Isotactic semicrystalline polymer; thermal transition study by DSC High yield; the MeOH-insoluble fraction has isotactic structure Stereochemistry of polymerization based on N M R Low MW polymer (970-4300) containing terminal unsaturation Polymer terminated with primary hydroxyl groups 621 620 622 623 624 625 625 Acetylene and hydrogep were generated through the polymerization The concentration of KOH did not affect the polymer yields Optically active polymer 626 Optically active polymer Chain transfer reaction involving the C — Η bond of the epoxide ring occurs Initiation mechanism depends both on the monomer and the metal complex used 629 630 627 628 631 Zn salts of xanthates, dithiocarbamates, thiocarboxylate High polymer 601 Et 2Zn-I 2 in THF Polymer was stabilized against oxidation by the ethylene sulfide-halogen adduct formed during polymerization reaction The polymer does not contain naphthalene or dihydronaphthalene groups in the chain Living polymer, kinetic study.

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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