Fluorine In Organic 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.

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

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.

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.

This volume brings together contributions by leading researchers covering a wide scope so characteristic of fluorine chemistry. It is a monograph of historical character comprising personalized accounts of progress and events in areas of particular interest. There is also much to interest and instruct chemists from other disciplines as a good proportion of the chapters contain a considerable amount of 'hard' referenced information relating to modern organic, organoelemental and inorganic chemistry. Historians of chemistry and technology will no doubt be tempted to dip into this book, and surely whoever addresses the task of commemorating Moissan's achievement at the 150-years stage will bless us all in some measure for its existence.

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

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.