Modern Fluoroorganic Chemistry (eBook)

Peer Kirsch was born in Herford, Germany, in 1965. He received his PhD in 1993 from the University of Heidelberg. After a postdoctoral stay at the Institute of Physical and Chemical Research (RIKEN) in Saitama, Japan, he joined the Liquid Crystal Division of Merck KGaA, Darmstadt, in 1995, where he held various positions in R&D and Business Development in both Germany and Japan. After obtaining his postdoctoral lecturing qualification (habilitation) in 2001, he began teaching at the universities of Bremen and Freiburg. His scientific interests - besides fluorine chemistry - lie in the areas of liquid crystals and organic and molecular electronics.

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

"... a well-produced book with attractive graphics, photos and schemes. Throughout the book, coloured electrostatic maps of small organofluorine compounds are used to illustrate charge distributions. These are effective as well as attractive. I would point any organic chemist to this book who wants to learn about and do some fluorine chemistry. It provides uncluttered descriptions and a clear orientation to the literature in this important area of the organic chemistry."
CHEMBIOCHEM - A European Journal of Chemical Biology