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9783540666899

Organofluorine Compounds

by ; ; ; ;
  • ISBN13:

    9783540666899

  • ISBN10:

    3540666893

  • Format: Hardcover
  • Copyright: 2000-03-01
  • Publisher: Springer Verlag
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Summary

In view of increasing interest in organofluorine compounds, this book was undertaken to describe biological and physical properties of organofluorine compounds, synthetic methods of these, their roles in pharmaceutical, agrochemical and material sciences. In particular, the book will emphasize on the usefulness of fluorination reaction, availability of fluorination agents, so that even graduate students who are unfamiliar to this field can understand and participate in this fascinating heteroatom chemistry.

Table of Contents

General Introduction
1(24)
Nature of Organofluorine Compounds
1(17)
Brief History
1(1)
Properties of the Fluorine Atom
2(1)
Fluorine Effects in Organic Compounds
3(7)
Properties of Fluoroorganic Compounds
10(3)
Properties of Perfluoroorganic Compounds
13(1)
Spectroscopic Properties
14(4)
Source of Fluorine
18(1)
Hydrogen Fluoride
18(1)
Fluorine Gas
18(1)
Toxicity of Fluorinating Reagents
19(6)
Hydrogen Fluoride and Fluorine Gas
19(1)
First-Aid Treatment
20(1)
Fluoroacetic Acid
21(4)
Reagents for Fluorination
25(52)
Electrophilic Flurorinating Reagents
25(14)
Fluorine Gas
25(3)
Xenon Difluoride
28(1)
Electrophilic Reagents Containing an O--F Bond
29(5)
Electrophilic Reagents Containing an N--F Bond
34(5)
Nucelophilic Fluorinating Reagents
39(17)
Hydrogen Fluoride and Derivatives
39(4)
Functional Group Transformation
43(5)
Fluoride Reagents
48(8)
Combination of an Electrophile and a Fluoride Reagent
56(10)
Halofluorination of Olefins and Acetylenes
56(2)
Thiofluorination and Selenofluorination of Olefins
58(1)
Nitrofluorination
59
Oxidative Fluorination
58(3)
Oxidative Desulfurization-Fluorination
61(4)
Oxidative Fluorination of Amines
65(1)
Electrochemical Fluorination
66(11)
Organofluorine Building Blocks
77(42)
Fluorine-Substituted Nucleophilic Reagents
77(22)
Alkylmetals
77(7)
Alkenylmetals
84(7)
Alkynylmetals
91(2)
Metal Enolates
93(6)
Fluorine-Substituted Electrophilic Reagents
99(4)
Fluorine-Substituted Radicals
103(4)
Fluorine-Substituted Carbenes
107(4)
Electrophilic Perfluoroalkylating Reagents
111(8)
(Perfluoroalkyl)aryliodonium Salts
111(1)
(Polyfluoroalkyl)aryliodonium Salts
112(1)
(Trifluoromethyl)chalcogenium Salts
113(6)
Reactions of C--F Bonds
119(18)
Fluorine Leaving Group
119(6)
1-Fluoro Sugars
119(2)
Aromatic Nucleophilic Substitution
121(4)
C--F Bond Activation by Metal Complexes
125(3)
Activation of an Aliphatic C--F Bond
125(1)
Activation of an Aromatic C--F Bond
126(2)
Interaction of Fluorine with a Proton or Metal
128(9)
Fluorine-Hydrogen Interaction
128(1)
Fluorine-Metal Interaction
129(8)
Biologically Active Organofluorine Compounds
137(46)
Fluorine Effect in Biological Activity
137(4)
Strategies for Design and Synthesis
141(3)
Structure-Activity Relationship
141(2)
Commercially Available Fluorinated Materials
143(1)
Fluorinated Amino Acids and Carbohydrates
144(10)
Amino Acids
144(4)
Protease Inhibitors
148(2)
Carbohydrates
150(1)
Nucleosides
151(3)
Fluorine-Containing Pharmaceuticals
154(12)
Prostanoids
154(3)
Vitamin D3
157(3)
Central Nervous System Agents
160(1)
Antibacterials and Antifungals
161(3)
β-Lactam Antibiotics
164(1)
Anesthetics
164(1)
Artificial Blood Substitutes
165(1)
18F-Labeled Tracers for Positron Emission Tomography
166(1)
Fluorine-Containing Agrochemicals
166(17)
Insecticides
167(6)
Herbicides
173(4)
Fungicides
177(6)
Fluorine-Containing Materials
183(52)
Fluorine Effect in Materials
183(5)
Boiling Points and Melting Points
184(2)
Solubility
186(1)
Surface Tension
186(1)
Refractive Index
187(1)
Viscosity
187(1)
Chlorofluorocarbons, Hydrochlorofluorocarbons, Hydrofluorocarbons, and Alternatives
188(8)
Brief History
188(3)
Production of Chlorofluorocarbons and Hydrochlorofluorocarbons
191(1)
Syntheses of CFC Alternatives
192(3)
Evaluation of Safety and Environmental Effects
195(1)
Alternatives to the Third Generation
196(1)
Fluorine-Containing Liquid Crystals
196(16)
Nematic Liquid Crystals
197(5)
Ferroelectric Liquid Crystals
202(7)
Antiferroelectric Liquid Crystals
209(3)
Fluorine-Containng Polymers
212(23)
Brief History
212(2)
Monomer Synthesis
214(2)
Fluoroplastics
216(4)
Fluoroelastomers
220(4)
Fluoropolymer Coatings
224(1)
Fluorosurfactants
225(3)
Fluorinated Membranes
228(7)
Fluorous Media
235(14)
Organic Reactions in Perfluorocarbons
235(2)
Fluorous Biphase Reactions
237(6)
Hydroformylation
237(2)
Oxidation
239(4)
Purification and Isolation by Phase Separation
243(6)
Organic Reactions with Fluorinated Reagents
249(16)
Fluoride Ion in Organic Synthesis
249(6)
Fluoride Base
249(1)
Desilylative Elimination and Deprotection
250(2)
Naked Anions and Fluorosilicates
252(3)
Trifluoroacetic Acid and Trifluoroperacetic Acid
255(2)
Trifluoroacetic Acid
255(1)
Trifluoroperacetic Acid
256(1)
Trifluoromethanesulfonic Acid and Derivatives
257(8)
Trifluoromethanesulfonic Acid
257(1)
Trimethylsilyl Trifluoromethanesulfonate
258(1)
Metal Trifluoromethanesulfonates
259(6)
Subject Index 265

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