NMR SPECTROSCOPY AND STEREOREGULARITY OF POLYMERS
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1 NMR SPECTROSCOPY AND STEREOREGULARITY OF POLYMERS Kei Matsuzaki, Toshiyuki Uryu, and Tetsuo Asakura with 148 Figures and 80 Tables JAPAN SCIENTIFIC SOCIETIES PRESS Tokyo KARGEH Basel-Freiburg-Paris-London-New York-New Delhi- Bangkok Singapore Tokyo Sydney
2 Contents PREFACE V ACKNOWLEDGEMENTS XV ABBREVIATIONS X\i I. NMR SPECTROSCOPY AND STEREOREGULARITY OF VINYL POLYMERS AND POLY(ALKYLENE OXIDE)S Chapter 1 Introduction Configuration of Polymers 'H NMR Spectra of Vinyl Polymers Deuteration of Monomers and Polymers Opening Mode of Vinyl Double Bonds and Ditactic Polymers Model Compounds C NMR Spectra of Vinyl Polymers C Side-Band Spectra Conformation of Vinyl Polymers Rate Processes Observed with NMR Spectroscopy Chapter 2 Polyolefins Polyethylene 25
3 Vlll 2.2 Polypropylene Poly(l-butene) Poly(l-pentene), Poly(l-hexene), Poly(l-heptene), Poly(loctene) andpoly(l-nonene) Poly(3-methyl-l-butene) 38 Chapter 3 Polydienes Polybutadiene Polyisoprene Polychloroprene 51 Chapter 4 Poly(methyl methacrylate) and Related Ester Derivatives Synthesis of Stereoregular Polymethacrylates 'H and 13 C NMR Spectroscdpy of Poly(methyl methacrylate) Stereoregularity of Related Ester Derivatives Polymerization of Optically Active Monomers and the Stereoregularity of Polymers.. ; Two Phase Polymerization of Poly(methyl methacrylate); Polymerization with Grignard Reagent as Catalyst Stereoregularity of Poly(methyl methacrylate) Obtained in Matrix Polymerization Optically Active Derivatives with Helical Structure..., 74 Chapter 5 Poly(methyl acrylate) and Related Ester Derivatives Synthesis of Stereoregular Polyacrylates Stereoregularity of Polyacrylates Determined by 'H NMR Spectroscopy C NMR Spectroscopy of Polyacrylates Double Bond Opening Mode of Acrylates in Polymerization Asymmetric Effects of Optically Active Side Groups in the Polymerization of Optically Active Acrylates 88
4 Contents ix 5.6 Conformation of Poly(methyl acrylate) 89 Chapter 6 Poly(a-chloroacrylate)s Introduction Synthesis of Stereoregular Poly(a-chloroacrylate)s 'H NMR Spectroscopy of Poly(a-chloroacrylate)s Stereocomplex Formation of Poly(a-chloroacrylate)s.. 97 Chapter 7 Poly(vinyl ether)s Introduction Synthesis of Stereoregular Poly(vinyl ether)s 'H NMR Spectroscopy of Poly(vinyl ether)s C NMR Spectroscopy of Poly(vinyl ether)s Stereochemistry in the Cationic Polymerization of Vinyl Ethers Optically Active Copolymers of Poly(vinyl ether)s Chapter 8 Poly(a-methyl vinyl ether)s 113 Chapter 9 Poly(vinyl ketone)s and Poly(isopropenyl ketone)s 'H and 13 C NMR Spectroscopy of Poly(vinyl ketone)s C NMR Spectroscopy of Poly(isopropenyl ketone)s Chapter 10 Polyacrylonitrile Synthesis of Polyacrylonitrile 'H NMR Spectroscopy of Polyacrylonitrile C NMR Spectroscopy of Polyacrylonitrile 128 Chapter 11 Polymethacrylonitrile Synthesis of Polymethacrylonitrile 131
5 X 11.2 'H NMR Spectroscopy and Stereoregularity of Polymethacrylonitrile C NMR Spectroscopy of Polymethacrylonitrile Chapter 12 Polystyrene and Its Derivatives Synthesis of Stereoregular Polystyrene 'H NMR Spectroscopy of Polystyrene C NMR Spectroscopy of Polystyrene Stereoregularity of Polystyrenes Obtained by Anionic Polymerization Stereoregularity of Polystyrenes Obtained with Butyllithium-Water Stereoregularity of Polystyrenes Obtained with Alfin Catalyst Stereoregularity of Polystyrenes Obtained with Cationic Catalysts Stereoregularity of Polystyrerfes Obtained by Radiation-Induced Polymerization Synthesis and Stereoregularity of Poly(methylstyrene)s Synthesis and Stereoregularity of Poly(methoxystyrene)s 152 Chapter 13 Poly(a-methylstyrene) Synthesis of Poly(oe-methylstyrene) ] H NMR Spectroscopy of Poly(a-methylstyrene) C NMR Spectroscopy of Poly(a-methylstyrene) Stereoregularity of Poly(a-methylstyrene) Obtained with Anionic Catalysts Stereoregularity of Poly(oe-methylstyrene) Prepared with Cationic Catalysts. 161 Chapter 14 Poly(vinylpyridine)s Synthesis of Poly(vinylpyridine)s 'H and 13 C NMR Spectroscopy of Poly(vinylpyridine)s. 163
6 Contents xi 14.3 Mechanism of Isotactic Polymerization of Poly(2- vinylpyridine) 168 Chapter 15 Poly(N-vinylcarbazole) Synthesis of Poly(N-vinylcarbazole) 'H and 13 C NMR Spectroscopy of Poly(N-vinylcarbazole) The Structure of Poly(N-vinylcarbazole) Obtained with Electron Acceptors as Catalysts 175 Chapter 16 Poly (vinyl acetate) Synthesis of Poly(vinyl acetate) 'H and 13 C NMR Spectroscopy of Poly(vinyl acetate) Chapter 17 Poly(isopropenyl acetate) Synthesis of Poly(isopropenyl acetate) 'H and 13 C NMR Spectroscopy of Poly(isopropenyl acetate) 182 Chapter 18 Polyethylene oxide) Synthesis of Polyethylene oxide) Conformation of Poly(ethylene oxide) Determined by 'H NMR spectroscopy Opening Mode in the Polymerization of Ethylene Oxide 193 Chapter 19 Poly(propylene oxide) Synthesis of Poly(propylene oxide) NMR Spectroscopy and Stereoregularity of Poly(propylene oxide) 199
7 xii Chapter 20 Poly(propenyl ether)s Introduction 'H and 13 C NMR Spectroscopy of Poly(j3-substituted vinyl ether)s Stereochemistry in the Process of Polymerization Chapter 21 Poly (vinyl alcohol) Synthesis of Poly (vinyl alcohol) 'H and 13 C NMR Spectroscopy of Poly(vinyl alcohol). 212 Chapter 22 Poly (vinyl chloride) Synthesis of Poly(vinyl chloride) 'H and 13 C NMR Spectroscopy of Poly(vinyl chloride). 216 Chapter 23 Factors Affecting Stereoregularity of Vinyl Polymers Radical Polymerization Cationic Polymerization Anionic Polymerization 225 II. REACTIONS CORRELATED TO THE STEREOREGULARITY OF POLYMERS Chapter 24 Thermal Reaction and Hydrolysis of Polymethacrylates and Polyacrylates Thermal Reaction and Anhydride Formation of Polymethacrylates Hydrolysis and Anhydride Formation of Polymethacrylates Hydrolysis and Anhydride Formation of Polyacrylates. 231
8 Contents xiii Chapter 25 Thermal Reaction of Poly(methyl vinyl ketone) and Poly(isopropenyl methyl ketone) Thermal Reaction of Poly (methyl vinyl ketone) Thermal Reaction of Poly(isopropenyl methyl ketone). 235 Chapter 26 Racemization of Polyacrylonitrile 239 III. NMR SPECTROSCOPY OF LIVING POLYMERS AND QUANTUM CHEMICAL ANALYSIS Chapter 27 Living Polystyrene NMR Spectroscopy of Polystyryl Anions and Their Model Compounds NMR Spectroscopy of Polystyryllithium and Its Model Compounds NMR Spectroscopy of Polystyrylpotassium and Its Model Compounds Effect of Counter Cation on the Excess Charge Distribution Effect of the Kind of Solvent on the Excess Charge Distribution Rotation of Ca-Cl Bond of Polystyryllithium and Its Model Compounds Quantum Chemical Treatment of Polystyryl Anions Spin-Lattice Relaxation Times T x of Living Anion Chapter 28 Living Poly(a-methylstyrene) 'H and 13 C NMR Spectroscopy of Living Poly(amethylstyrene) Quantum Chemical Calculation of Poly(a-methylstyryl) Anion Rotation of Ca-C 1 Bond of Poly (a-methylstyryl) Lithium 257
9 xiv Chapter 29 Living Poly(methylstyrene)s Introduction NMR Spectroscopy of Living Poly(o-methylstyrene) and Its Model Compound NMR Spectroscopy of Living Poly(m-methylstyrene) and Its Model Compound NMR Spectroscopy of Living Poly(p-methylstyrene) Chapter 30 Living Poly(o-methoxystyrene) 265 SUBJECT INDEX ABOUT THE AUTHORS 2 7 7
Supported in part by the Ministry of Education, Science, Sports and Culture under Grant-in-Aid for Publication of Scientific Research Result.
NMR SPECTROSCOPY AND STEREOREGULARITY OF POLYMERS NMR SPECTROSCOPY AND STEREORHULARITY OF POLYMERS Kei Matsuzaki, Toshiyuki Uryu, and Tetsuo Asakura with 148 Figures and 80 Tables JAPAN SCIENTIFIC SOCIETIES
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