The introduction of carbon-fluorine bonds into organic compounds can profoundly influence their chemical and physical properties when compared to their non-fluorine-containing analogues, leading to a range of man-made materials with highly desirable properties. These molecules are of interest across the wide spectrum of industrial and academic organic chemistry, from pharmaceuticals, through fine and specialty chemicals to polymers. From Prozac to Teflon, many of the most important products of the chemical and life-science industries rely on organic fluorine chemistry for their useful properties. This book covers both the preparative methodologies and chemical properties of partially and highly fluorinated organic systems.

The present book is essentially based on the lectures on the chemistry of organic compounds of fluorine that I gave in 1969 at Virginia Polytechnic Institute in Blacksburg, Virginia, as a graduate course. References to material published to the end of 1969 are included. The book is primarily meant to provide the background for such a course, and, at the same time, to be a brief survey of recent knowledge in, and an introduction to deeper study of, this area of chemistry, which has been treated in a number of com prehensive monographs. I would like to thank Professor S. C. Cohen, Syracuse University, for the compilation of the data on mass spectra and nuclear magnetic res onance spectra, and my son, Tomas Hudlicky, and my daughter, Eva Hudlickci, for their help with the indexes. MILOS HUDLICKY February 13, 1970 Virginia Polytechnic Institute and State University Blacksburg, Virginia vii Contents CHAPTER 1. Introduction ......................................................... 1 Development of Fluorine Chemistry ......................................... .

Organic and Inorganic Fluorine Chemistry provides an introduction to fluorine chemistry and an overview of the most important fluorinated compounds and general preparation techniques. The book is divided into three parts, covering general aspects, inorganic fluorides and fluoroorganic compounds. The inorganic part presents the most important element fluorides and oxyfluorides, their preparation as well as their most characteristic properties. The organic section focuses on the different types of fluorination and the corresponding reagents. The application of these techniques is discussed for many different types of substrates. The book addresses advanced students in chemistry as well as researchers in academia and industry. The readers will benefit from a large number of original references which give access to further information. In addition, study questions at the end of each chapter will help to repeat and internalise the most important aspects.

The replacement of hydrogen with fluorine in organic molecules canprofoundly influence their chemical and physical properties,leading to a range of compounds with highly desirable properties.These molecules are of interest across the wide spectrum ofindustrial and academic organic chemistry, so that organofluorinechemistry is economically highly important. Organofluorine Chemistry will help chemists to develop a systematicknowledge of the chemistry of fluorine with a view towards itsapplication in the design of new reactions and syntheses, and thecreation of novel fluorinated molecules and materials. With initialchapters focusing on why fluorine creates such unique properties inorganic compounds, the book then covers general reactions offluorine. Coverage is chosen from the recent research literature,concentrating on the development of novel bioactive compounds andcatalytic ligands, and explaining, in the context of the initialchapters, how and why fluorine is so effective. With a finalchapter covering the general synthetic chemistry of organofluorinecompounds, the book is a cohesive summary of the fundamentalprincipals of organofluorine chemistry.

In this handbook, Peer Kirsch clearly shows that this exciting field is no longer an exotic area of research. Aimed primarily at synthetic chemists wanting to gain a deeper understanding of the fascinating implications of including the highly unusual element fluorine in organic compounds, the main part of the book presents a wide range of synthetic methodologies and the experimental procedures selected undeniably show that this can be done with standard laboratory equipment. To round off, the author looks at fluorous chemistry and the applications of organofluorine compounds in liquid crystals, polymers and more besides. This long-awaited book represents an indispensable source of high quality information for everyone working in the field.

In the fields of biologically active materials and functional materials, fluorinated organic materials are becoming a focus of significant interest. Over the past decade synthetic methodologies and reagents in fluorine chemistry have been developed, especially stereocontrolled synthetic methods, enzymatic resolution to synthesize enantiomers, fluoromethylated reagents, and fluorination reagents. These methods have contributed to the opening of new pathways for fluorinated materials. However, few fluorinated materials have been put to commercial use. Furthermore, there remain problems to be solved, such as the handling of the materials, availability of reagents and selectivity (stereo-, regio-, and/or chemoselectivity). Research chemists, technical engineers, and graduate students in all branches of chemistry, pharmaceutics, and material science interested in fluorinated materials need to know detailed experimental procedures of how to synthesize the target fluorinated materials. This volume summarizes the chemical and microbial methods for obtaining functionalized fluorinated materials for use as building blocks; detailed experimental methods (reaction conditions, solvent, temperature, handling techniques, etc.); and the stereoview (possible absolute configuration) of the structures with spectral data. Mono-, di-, tri-, and polyfluorinated materials derived from fluorinating agents, fluoromethylated reagents and building blocks are summarized. A chemical name index, molecular formula index, and reagent index are also included. The publication of this monograph will provide access to the enormous possibilities in fluorine chemistry, biological material chemistry, and functionalized material chemistry.

Following its well-received predecessor, this book offers an essential guide to chemists for understanding fluorine in spectroscopy. With over 1000 compounds and 100 spectra, the second edition adds new data – featuring fluorine effects on nitrogen NMR, chemical shifts, and coupling constants. • Explains how to successfully incorporate fluorine into target molecules and utilize fluorine substituents to structurally characterize organic compounds • Includes new data on nitrogen NMR, focusing on N-15, to portray the influence of fluorine upon nitrogen NMR chemical shifts and coupling constants • Expands on each chapter from the first edition with additional data and updated discussion from recent findings • "The flawless ordering of material covered in this stand-alone volume is such that information can be found very easily." – Angewandte Chemie review of the first edition, 2010

Fluorine Chemistry, Volume IV provides an extensive survey and discussion on the physiological properties of fluoride ion and substances capable of producing it in aqueous solution. This book elaborates the detrimental effects of excessive fluoride ingestion, through the beneficial effects of optimal amounts, to recognized detrimental effects, such as dental caries accompanied by suboptimal fluoride intake. Fluoride metabolism is discussed in detail, including the capacity for storage of fluoride by the bones and rates of excretion of fluoride from the body. This text also covers the relation of fluoride ion to the health of teeth and bones. This publication is a good source for chemists and clinicians intending to acquire knowledge of the biological effects of fluoride.