Organofluorine compounds : chemistry and applications

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Organofluorine compounds : chemistry and applications / Tamejiro Hiyama ; with contributions by Tamejiro Hiyama, Kiyoshi Kanie ... [et al.]

資料種別:

図書[東工大目次DB]

出版情報:

Berlin ; Tokyo : Springer, c2000

形態:

xii, 272 p. ; 25 cm

著者名:

ISBN:

9783540666899 [3540666893]

書誌ID:

BA46846451

子書誌情報

フルテキスト

所蔵情報

他の版・巻

書誌詳細

注記:

Includes bibliographical references and index

主題:

Organofluorine compounds

言語:

英語

目次情報:

Chapter 1 General Introduction 1

1.1 Nature of Organofluorine Compounds 1

1.1.1 Brief History 1

1.1.2 Properties of the Fluorine Atom 2

1.1.3 Fluorine Effects in Organic Compounds 3

1.1.4 Properties of Fluoroorganic Compounds 10

1.1.5 Properties of Perfluoroorganic Compounds 13

1.1.6 Spectroscopic Properties 14

1.2 Source of Fluorine 18

1.2.1 Hydrogen Fluoride 18

1.2.2 Fluorine Gas 18

1.3 Toxicity of Fluorinating Reagents 19

1.3.1 Hydrogen Fluoride and Fluorine Gas 19

1.3.2 First-Aid Treatment 20

1.3.3 Fluoroacetic Acid 21

Chapter 2 Reagents for Fluorination 25

2.1 Electrophilic Fluorinating Reagents 25

2.1.1 Fluorine Gas 25

2.1.2 Xenon Difluoride 28

2.1.3 Electrophilic Reagents Containing an O-F Bond 29

2.1.4 Electrophilic Reagents Containing an N-F Bond 34

2.2 Nucelophilic Fluorinating Reagents 39

2.2.1 Hydrogen Fluoride and Derivatives 39

2.2.2 Functional Group Transformation 43

2.2.3 Fluoride Reagents 48

2.3 Combination of an Electrophile and a Fluoride Reagent 56

2.3.1 Halofluorination of Olefins and Acetylenes 56

2.3.2 Thiofluorination and Selenofluorination of Olefins 58

2.3.3 Nitrofluorination 59

2.3.4 Oxidative Fluorination 58

2.3.5 Oxidative Desulfurization-Fluorination 61

2.3.6 Oxidative Fluorination of Amines 65

2.4 Electrochemical Fluorination 66

Chapter 3 Organofluorine Building Blocks 77

3.1 Fluorine-Substituted Nucleophilic Reagents 77

3.1.1 Alkylmetals 77

3.1.2 Alkenylmetals 84

3.1.3 Alkynylmetals 91

3.1.4 Metal Enolates 93

3.2 Fluorine-Substituted Electrophilic Reagents 99

3.3 Fluorine-Substituted Radicals 103

3.4 Fluorine-Substituted Carbenes 107

3.5 Electrophilic Perfluoroalkylating Reagents 111

3.5.1 (Perfluoroalkyl)aryliodonium Salts 111

3.5.2 (Polyfluoroalkyl)aryliodonium Salts 112

3.5.3 (Trifluoromethyl)chalcogenium Salts 113

Chapter 4 Reactions of C-F Bonds 119

4.1 Fluorine Leaving Group 119

4.1.1 1-Fluoro Sugars 119

4.1.2 Aromatic Nucleophilic Substitution 121

4.2 C-F Bond Activation by Metal Complexes 125

4.2.1 Activation of an Aliphatic C-F Bond 125

4.2.2 Activation of an Aromatic C-F Bond 126

4.3 Interaction of Fluorine with a Proton or Metal 128

4.3.1 Fluorine-Hydrogen Interaction 128

4.3.2 Fluorine-Metal Interaction 129

Chapter 5 Biologically Active Organofluorine Compounds 137

5.1 Fluorine Effect in Biological Activity 137

5.2 Strategies for Design and Synthesis 141

5.2.1 Structure-Activity Relationship 141

5.2.2 Commercially Available Fluorinated Materials 143

5.3 Fluorinated Amino Acids and Carbohydrates 144

5.3.1 Amino Acids 144

5.3.2 Protease Inhibitors 148

5.3.3 Carbohydrates 150

5.3.4 Nucleosides 151

5.4 Fluorine-Containing Pharmaceuticals 154

5.4.1 Prostanoids 154

5.4.2 Vitamin D3 157

5.4.3 Central Nervous System Agents 160

5.4.4 Antibacterials and Antifungals 161

5.4.5 βーLactam Antibiotics 164

5.4.6 Anesthetics 164

5.4.7 Artificial Blood Substitutes 165

5.4.8 18F-Labeled Tracers for Positron Emission Tomography 166

5.5 Fluorine-Containing Agrochemicals 166

5.5.1 Insecticides 167

5.5.2 Herbicides 173

5.5.3 Fungicides 177

Chapter 6 Fluorine-Containing Materials 183

6.1 Fluorine Effect in Materials 183

6.1.1 Boiling Points and Melting Points 184

6.1.2 Solubility 186

6.1.3 Surface Tension 186

6.1.4 Refractive Index 187

6.1.5 Viscosity 187

6.2 Chlorofluorocarbons, Hydrochlorofluorocarbons, Hydrofluorocarbons, and Alternatives 188

6.2.1 Brief History 188

6.2.2 Production of Chlorofluorocarbons and Hydrochlorofluorocarbons 191

6.2.3 Syntheses of CFC Alternatives 192

6.2.4 Evaluation of Safety and Environmental Effects 195

6.2.5 Alternatives to the Third Generation 196

6.3 Fluorine-Containing Liquid Crystals 196

6.3.1 Nematic Liquid Crystals 197

6.3.2 Ferroelectric Liquid Crystals 202

6.3.3 Antiferroelectric Liquid Crystals 209

6.4 Fluorine-Containing Polymers 212

6.4.1 Brief History 212

6.4.2 Monomer Synthesis 214

6.4.3 Fluoroplastics 216

6.4.4 Fluoroelastomers 220

6.4.5 Fluoropolymer Coatings 224

6.4.6 Fluorosurfactants 225

6.4.7 Fluorinated Membranes 228

Chapter 7 Fluorous Media 235

7.1 Organic Reactions in Perfluorocarbons 235

7.2 Fluorous Biphase Reactions 237

7.2.1 Hydroformylation 237

7.2.2 Oxidation 239

7.3 Purification and Isolation by Phase Separation 243

Chapter 8 Organic Reactions with Fluorinated Reagents 249

8.1 Fluoride Ion in Organic Synthesis 249

8.1.1 Fluoride Base 249

8.1.2 Desilylative Elimination and Deprotection 250

8.1.3 Naked Anions and Fluorosilicates 252

8.2 Trifluoroacetic Acid and Trifluoroperacetic Acid 255

8.2.1 Trifluoroacetic Acid 255

8.2.2 Trifluoroperacetic Acid 256

8.3 Trifluoromethanesulfonic Acid and Derivatives 257

8.3.1 Trifluoromethanesulfonic Acid 257

8.3.2 Trimethylsilyl Trifluoromethanesulfonate 258

8.3.3 Metal Trifluoromethanesulfonates 259

Subject Index 265

Chapter 1 General Introduction 1

1.1 Nature of Organofluorine Compounds 1

1.1.1 Brief History 1

1.1.2 Properties of the Fluorine Atom 2

1.1.3 Fluorine Effects in Organic Compounds 3

1.1.4 Properties of Fluoroorganic Compounds 10

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