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The book summarizes and gives a critical analysis of the literature on the use of reactive covalent fluorides (organic and inorganic) for the synthesis of fluoroorganic compounds. New methods of using SF4 for the fluorination of complex polyfunctional organic compounds are described. The prospects are shown for the selective fluorinations of complex compounds with non-traditional fluorinating agents (halogen fluorides, XeF2, fluorosulphuranes, N-F- and O-F-containing compounds). The book gives recommendations for the practical use of these fluorides, and typical synthetic procedures. It introduces the beginner to modern methods of fluorination and helps qualified scientists and technologists to choose the optimal methods of synthesis. Using the fluorinating agents described in this book, it is possible to synthesize various fluorine-containing substances.
Academia and industry join forces in Aromatic Fluorination, as an expert from each domain contributes to this new text on fluorination of carbocyclic and heterocyclic rings. The book begins with a discussion of fluorine's unique combination of properties, including size, electronic effects, and hydrophobicity, as well as the historical development of its product applications. It explains methods for introducing fluorine into an aromatic ring, focusing on nucleophilic fluorine transfer reactions. The role of catalysts, solvents, and other variables are examined, and the scope and limitations of the methods are discussed. Of particular interest to those working in non-specialist laboratories, Aromatic Fluorination includes detailed descriptions of the new electrophilic routes to fluoroaromatics, in addition to traditional routes and alternative methods involving radical chemistry. Because one of the most important fluorine-containing substituent is CF3, the book explains routes to benzotrifluorides (ArCF3), including traditional industrial methods and modern alternatives employing C-1 halofluorocarbons and other fluoroaliphatics. An alternative to CF3 is CF3S, and several methods of synthesizing aromatic CF3S-containing molecules are described. Since the successful development and diverse applications of aromatic fluorine compounds have led to the search for new compounds and novel substituents, the incorporation of other substituents is also explored. Aromatic Fluorination concludes with discussion of the factors responsible for the successful development of pharmaceutical, agrochemical and liquid crystal applications and the potential for applications in high-performance polymers and other areas. This section also describes in detail important industrial aromatic fluorination processes and the relative merits of different process technologies and their costs.
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.
In view of increasing interest in organofluorine compounds, this book was undertaken to describe biological and physical properties of organofluorine compounds, synthetic methods of these, their roles in pharmaceutical, agrochemical and material sciences. In particular, the book will emphasize on the usefulness of fluorination reaction, availability of fluorination agents, so that even graduate students who are unfamiliar to this field can understand and participate in this fascinating heteroatom 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 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.