Modern Fluoroorganic Chemistry

The second edition of this classic reference work has been completely revised and updated, as well as being enlarged by 20% to reflect the latest developments in synthetic organic fluorine chemistry, taking into account new applications in materials science and medicinal chemistry.

The new developments in transition-metal-catalyzed methods for the introduction of fluorine and fluorinated groups are discussed. In addition, new chapters have been added on such important applications as organic electronics (OLEDs) and fluorinated dyes. Appendices containing synthetic procedures and conversions round off this comprehensive work.

This work is a valuable reference for fluorine chemists that also provides nonspecialists with an introduction to the field.

From reviews of the first edition:
''... a well-produced book with attractive graphics, photos and schemes. Throughout the book, coloured electrostatic maps of small
organofluorine compounds are used toillustrate 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

Autorentext
Peer Kirsch is the Director of Emerging Technologies at Merck KGaA in Darmstadt, Germany. Having obtained his PhD in chemistry at Heidelberg University and the Max Planck Institute for Medical Research working with Prof. Dr. Heinz A. Staab in 1993, he spent two years as a postdoctoral researcher at the Institute of Physical and Chemical Research (RIKEN) in Wako, Japan, before he joined Merck in 1995. He worked on the design and synthesis of liquid crystals for LCD applications for 10 years, with a strong focus on fluoroorganic synthesis and computational property prediction. From 2005 to 2010 he worked for Merck Ltd. Japan in various functions. Since 2009 Peer Kirsch is a visiting professor at the University of Bremen and he teaches also at the University of Freiburg since 2011. He has authored more than 45 scientific publications as well as more than 140 patents. His main research interests include the application of fluoroorganic chemistry, molecular modelling and combinatorial methods for the design and synthesis of highly fluorinated liquid crystals and other advanced materials.

Inhalt
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