Organic Fluorine Chemistry

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 ......................................... .

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.

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.

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.

Provides complete coverage of the chemistry of organic fluorine compounds. Topics include fluorinating agents, fluorination processes, reactions of fluorinated compounds, modern analytical methods, and properties and applications of fluorinated compounds. Offers a critical review of the literature and provides over 4,500 references. Updates the 1976 volume Chemistry of Organic Fluorine Compounds.

This book is a synthesis of two of Hudlicky's earlier books outlining the many unpredictable properties of fluorine and its compounds that are not analogous to the properties of any other halogens and their compounds. It is divided into two separate sections, the first presenting peculiar reactions as problems to be solved. Each reaction can be analyzed in the lab without the help of the second section, however if a solution is not easily reached, the second section provides discussion of the problems, outlining the products of the reactions and their mechanisms. Among the 105 reactions outlined are the introduction of fluorine into organic molecules, reduction and oxidation of fluorine compounds, reactions of fluorocompounds with halogens and their derivatives, nitration, acid catalyzed reactions, organometallic syntheses, and pyrolyses. The reactions are documented in the experimental material of the earlier volumes and will be important background knowledge for anyone working in organic chemistry.