Modern Fluoroorganic Chemistry - Synthesis, Reactivity, Applications

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

List of contents

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 FluorinationElectrochemical 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 CompoundsHALOFLUOROCARBONS, 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 PROCEDURESSelective 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 Me3SiCF3Transition Metal-Mediated Aromatic Perfluoroalkylation Copper-Mediated Introduction of the Trifluoromethylthio Group Substitution Reactions on Fluoroolefins and Fluoroarenes Reactions with DifluoroenolatesAPPENDIX B: INDEX OF SYNTHETIC CONVERSIONSINDEX

About the author

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.

Summary

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

Report

"... 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

Product details

• Authors: Peer Kirsch
• Publisher: Wiley-VCH
• Languages: English, German
• Product format: Hardback
• Released: 31.03.2015
• EAN: 9783527331666
• ISBN: 978-3-527-33166-6
• No. of pages: 338
• Dimensions: 177 mm x 249 mm x 25 mm
• Weight: 986 g
• Illustrations: 34 SW-Abb., 19 Farbabb., 29 Tabellen
• Subjects: Natural sciences, medicine, IT, technology > Chemistry > Organic chemistry; Chemie, Organische Chemie, ORGANIC CHEMISTRY, Katalyse, chemistry, Catalysis, Materialwissenschaften, Materials science, Pharmaceutical & Medicinal Chemistry, Pharmazeutische u. Medizinische Chemie, Organic Electronics, Organische Elektronik, Fluorverbindungen