Organic Fluorine Chemistry

Organic Fluorine Chemistry

by Milos Hudlicky

Paperback(Softcover reprint of the original 1st ed. 1971)

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Product Details

ISBN-13: 9781461586449
Publisher: Springer US
Publication date: 03/28/2012
Edition description: Softcover reprint of the original 1st ed. 1971
Pages: 200
Product dimensions: 5.98(w) x 9.02(h) x 0.02(d)

Table of Contents

1. Introduction.- Development of Fluorine Chemistry.- Handling of Fluorine, Hydrogen Fluoride, and Fluorine Compounds.- Equipment and Apparatus.- 2. Fluorinating Agents.- Hydrogen Fluoride.- Fluorine.- Inorganic Fluorides.- Organic Fluorides.- 3. Nomenclature of Organic Fluorine Compounds.- 4. Introduction of Fluorine into Organic Compounds.- Addition of Hydrogen Fluoride to Olefins.- Addition of Hydrogen Fluoride to Acetylenes and Other Unsaturated Systems.- Addition of Fluorine to Olefins.- Addition of Fluorine to Other Unsaturated Systems.- Addition of Halogen Fluorides and Organic Fluorides to Olefins.- Replacement of Hydrogen by Fluorine.- Replacement of Halogens by Fluoride.- Replacement by Means of Hydrogen Fluoride.- Replacement by Means of Antimony Fluorides.- Replacement by Means of Silver Fluoride.- Replacement by Means of Mercury Fluorides.- Replacement by Means of Potassium Fluoride.- Replacement by Means of Other Fluorides.- Replacement of Oxygen by Fluorine.- Cleavage of Ethers and Epoxides.- Cleavage of Sulfonic Esters.- Replacement of Hydroxylic Group by Fluorine.- Replacement of Carbonyl Oxygen by Fluorine.- Conversion of Carboxylic Group to Trifluoromethyl Group.- Replacement of Nitrogen by Fluorine.- 5. Analysis of Organic Fluorine Compounds.- Physical Methods of Analysis of Fluorine Compounds or Their Mixtures.- Infrared Spectroscopy.- Mass Spectroscopy.- Nuclear Magnetic Resonance Spectroscopy.- Separation of Mixtures and Purification of Components.- Qualitative Tests for Fluorine.- Detection of Elemental Fluorine.- Detection of Fluoride Ion.- Detection of Fluorine in Organic Compounds.- Quantitative Determination of Fluoride.- Volumetric Determination.- Determination Using Fluoride Membrane Electrode.- Mineralization of Fluorine in Organic Compounds.- Decomposition with Alkalies.- Combustion in Oxygen.- Determination of Other Elements in Organic Fluorine Compounds.- Special Analyses.- 6. Properties of Organic Fluorine Compounds.- Physical Properties.- Melting Points.- Boiling Points.- Density.- Refractive Index.- Dielectric Constant.- Surface Tension.- Viscosity.- Solubility.- Physicochemical Properties.- Biological Properties.- 7. Practical Applications of Organic Fluorine Compounds.- Refrigerants, Propellants, and Fire Extinguishers.- Plastics and Elastomers.- Monomers.- Polymerization.- Processing of Polymers.- Applications of Plastics and Elastomers.- Fluorinated Compounds as Pharmaceuticals.- Other Uses of Fluorinated Compounds.- 8. Reactions of Organic Fluorine Compounds.- Factors Governing the Reactivity of Organic Fluorine Compounds.- Inductive Effect.- Hyperconjugation.- Mesomeric Effect.- Steric Effects.- Important Features in the Reactivity of Organic Fluorine Compounds.- Reduction.- Catalytic Hydrogenation.- Reduction with Complex Hydrides.- Reduction with Metals and Metallic Compounds.- Reduction with Organic Compounds.- Oxidation.- Oxidations with Oxygen.- Oxidations with Oxidative Reagents.- Oxidations of Fluoro-olefins.- Oxidations of Fluorinated Aromatics.- Oxidation of Nitrogen and Sulfur Compounds.- Anodic Oxidation.- Electrophilic Reactions.- Halogenation.- Addition of Halogens across Multiple Bonds.- Replacement of Hydrogen by Halogens.- Cleavage of the Carbon Chain by Halogens.- Addition of Hydrogen Halides across Multiple Bonds.- Replacement of Oxygen- and Nitrogen-Containing Functions by Halogens.- Replacement of Fluorine by Other Halogens.- Nitration.- Nitrosation.- Sulfonation.- Acid-Catalyzed Syntheses (Friedel-Crafts Reaction).- Acid-Catalyzed Additions.- Acid-Catalyzed Substitutions.- Nucleophilic Substitutions.- Esterification and Acetalization.- Hydrolysis.- Hydrolysis of Nonfluorinated Parts of Fluorinated Molecules.- Hydrolytic Displacement of Single Fluorine Atoms.- Hydrolysis of Difluoromethylene Group.- Hydrolysis of Trifluoromethyl Group.- Hydrolysis of Perfluoro Compounds.- Fluoroform Reaction.- Alkylations.- Alkylations at Oxygen.- Alkylations at Sulfur.- Alkylations at Nitrogen and Phosphorus.- Alkylations at Carbon.- Arylations.- Arylations at Oxygen.- Arylations at Sulfur.- Arylations at Nitrogen.- Arylations at Carbon.- Acylations.- Acylations at Oxygen.- Acylations at Sulfur.- Acylations at Nitrogen.- Acylations at Carbon.- Syntheses with Organometallic Compounds.- The Grignard Syntheses.- Grignard Reagents as Organic Substrate.- Fluorinated Grignard Reagents.- Perfluorinated Grignard Reagents.- Organolithium Compounds.- Organolithium Compounds as Organic Substrate.- Fluorinated Organolithium Compounds.- Perfluorinated Organolithium Compounds.- Organozinc Compounds.- Organomercury Compounds.- Organocopper Compounds.- Organometalloids.- Base-Catalyzed Condensations.- Additions.- Nucleophilic Additions to Fluorinated Olefins.- Additions of Alcohols and Phenols.- Additions of Mercaptans and Thiophenols.- Additions of Ammonia and Amines.- Free-Radical-Type Additions.- Linear Additions.- Cycloadditions.- Formation of Three-Membered Rings.- Formation of Four-Membered Rings.- Formation of Five-Membered Rings.- Formation of Six-Membered Rings (Diels-Alder Reaction).- Eliminations.- Dehalogenations.- Dehydrohalogenations.- Decarboxylations.- Dehydration.- Molecular Rearrangements.- Pyroreactions.- 9. Fluorinated Compounds as Chemical Reagents.- References.- Author Index.

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