Selectfluor

Abstract: PREFACE TO THE SECOND EDITION PREFACE TO THE FIRST EDITION INTRODUCTION Why Organofluorine Chemistry? History The Basic Materials The Unique Properties of Organofluorine Compounds PART I: Synthesis of Complex Organofluorine Compounds INTRODUCTION OF FLUORINE Perfluorination and Selective Direct Fluorination Electrochemical Fluorination (ECF) Nucleophilic Fluorination Synthesis and Reactivity of Fluoroaromatic Compounds Transformations of Functional Groups "Electrophilic" Fluorination PERFLUOROALKYLATION Radical Perfluoroalkylation Nucleophilic Perfluoroalkylation "Electrophilic" Perfluoroalkylation Difluorocarbene and Fluorinated Cyclopropanes SELECTED FLUORINATED STRUCTURES AND REACTION TYPES Difluoromethylation and Halodifluoromethylation The Perfluoroalkoxy Group The Perfluoroalkylthio Group and Sulfur-Based Super-Electron-Withdrawing Groups The Pentafluorosulfanyl Group and Related Structures THE CHEMISTRY OF HIGHLY FLUORINATED OLEFINS Fluorinated Polymethines Fluorinated Enol Ethers as Synthetic Building Blocks PART II: Fluorous Chemistry FLUOROUS CHEMISTRY Fluorous Biphase Catalysis FLUOROUS SYNTHESIS AND COMBINATORIAL CHEMISTRY Fluorous Synthesis Separation on Fluorous Stationary Phases Fluorous Concepts in Combinatorial Chemistry PART III: Applications of Organofluorine Compounds HALOFLUOROCARBONS, HYDROFLUOROCARBONS, AND RELATED COMPOUNDS Polymers and Lubricants Applications in the Electronics Industry Fluorinated Dyes Liquid Crystals for Active Matrix Liquid Crystal Displays Fluorine in Organic Electronics PHARMACEUTICALS AND OTHER BIOMEDICAL APPLICATIONS Why Fluorinated Pharmaceuticals? Lipophilicity and Substituent Effects Hydrogen Bonding and Electrostatic Interactions Stereoelectronic Effects and Conformation Metabolic Stabilization and Modulation of Reaction Centers Bioisosteric Mimicking Mechanism-Based "Suicide" Inhibition Fluorinated Radiopharmaceuticals Inhalation Anesthetics Blood Substitutes and Respiratory Fluids Contrast Media and Medical Diagnostics Agricultural Chemistry APPENDIX A: TYPICAL SYNTHETIC PROCEDURES Selective Direct Fluorination Hydrofluorination and Halofluorination Electrophilic Fluorination with F-TEDA - BF4 (Selectfluor) Fluorinations with DAST and BAST (Deoxofluor) Fluorination of a Carboxylic Acid with Sulfur Tetrafluoride Generation of a Trifluoromethoxy Group by Oxidative Fluorodesulfuration of a Xanthogenate Oxidative Alkoxydifluorodesulfuration of Dithianylium Salts Electrophilic Trifluoromethylation with Umemoto's Reagents Nucleophilic Trifluoromethylation with Me3SiCF3 Transition Metal-Mediated Aromatic Perfluoroalkylation Copper-Mediated Introduction of the Trifluoromethylthio Group Substitution Reactions on Fluoroolefins and Fluoroarenes Reactions with Difluoroenolates APPENDIX B: INDEX OF SYNTHETIC CONVERSIONS INDEX