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.

This two-volume work combines comprehensive information on the chemistry of the fluorinated heterocycles. The material has been divided such that the first volume is dedicated to 5-membered fluorinated heterocycles and macrocycles, while the second volume combines data connected with the chemistry of fluorine containing 6-membered heterocycles. Both volumes will be of interest to synthetic organic chemists in general, and particularly for those colleagues working in the fields of heterocyclic-compound chemistry, materials chemistry, medicinal chemistry, and fluorine chemistry. All information is presented and classified clearly to be effective source for broad auditory of chemists. It will be interesting for scientists working in the field of inorganic and coordination chemistry. Fluorinated heterocycles are becoming increasingly important in many areas including the pharmaceutical industry, materials science and agriculture. The presence of fluorine can result in substantial functional changes in the biological as well as physicochemical properties of organic compounds. Incorporation of fluorine into drug molecules can greatly affect their physicochemical properties, such as bond strength, lipophilicity, bioavailability, conformation, electrostatic potential, dipole moment, pKa etc. as well as pharmacokinetic properties, such as tissue distribution, rate of metabolism and pharmacological properties, such as pharmacodynamics and toxicology.

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.

Coverage For some time, we have contemplated a comprehensive review of the structures and force fields of the binary fluorides. This bibliography of 1498 references marks the first step of that effort. We are pub lishing this material now rather than waiting until the review is complete some two years hence because we believe that the information already accumulated will be of immediate use to a broad spectrum of researchers. Anyone ambitious enough to read through all the articles on binary fluorides will find that the struc tures and force fields of many of these molecules are at present unknown. For example, it has not been clearly established to which point group(s) the lanthanide trifluorides should be assigned. There remain interesting problems relating to the role of Jahn-Teller and pseudo-Jahn-Teller distortions in some of the transition metal fluorides such as VF , MoF , ReF , and ReF , to name only a few. One s s 6 7 also finds fascinating examples of large-amplitude motions, or pseudorotations, as they are often called, in such molecules as XeF 6, I F 7, and PF 5' For those binary fluorides whose equilibrium geometries are precisely known, there still exists the problem of accurately determining the harmonic force field. In a few cases, most notably the Group VA trifluorides, there has been some attempt made at extracting the cubic and quartic contributions to the force field.

Fluorine: A Paradoxical Element, Volume Five, deals with the link between fluorine, humanity and the environment. It is divided into three main sections, including i) The history and developmental stages of fluorinated products, ii) Awareness of its importance in our environment, and iii) Recent contributions of fluoride products in medicine, pharmacy and our daily lives. Made engaging through interesting figures and accessible language, and written by a leading expert, Professor Tressaud, the book supports the work of scientists working in materials, toxicology and environmental science. It complements the author's edited series, Progress in Fluorine Science, covering recent advances. - Describes background and contextual information regarding the history, development of understanding, and applications of this important element - Explores the impacts of fluorine, both positive and negative, in the environment and biological systems - Includes applied, real-world information from agencies, such as CNRS, NASA, HWS and DOH

This is the first ACS symposium series book solely devoted to fluorinated heterocyclic compounds. Its contents encompasses all aspects of chemistry and applications of fluoroheterocycles including synthesis, biological activity, computational and medicinal research covering all major classes of heterocycles as well as popular fluorine-containing fragments.