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Free radical reactions have become increasingly important and a very attractive tool in organic synthesis in the last two decades, due to their powerful, selective, specific, and mild reaction abilities. Advanced Free Radical Reactions for Organic Synthesis reviews information on all types of practical radical reactions, e.g. cyclizations, additions, hydrogen-atom abstractions, decarboxylation reactions. The book usefully provides experimental details for the most important reactions as well as numerous references to the original literature. By covering both the fundamentals and synthetic applications it is therefore suitable for both new and experienced researchers, chemists, biochemists, natural product chemists and graduate students. This title is the definitive guide to radical chemistry for all scientists. Introduces and reviews the use of radicals to perform synthetic transformations Practical details are provided for the most important methods Numerous references to the original literature
Introduction and some general concepts. -- General principles: chain reactions based on stannane chemistry. -- Further chain reactions of stannanes. -- Organo-silicon, -germanium, and -mercury hydrides. -- The Barton decarboxylation and related reactions. -- Atom and group transfer reactions. -- The persistent radical effect: non-chain processes. -- Redox processes. -- Some concluding remarks.
Written for both the experienced practitioner and the newcomer, this book provides essential guidance to the practical aspects of free radical chain reactions. The book presents tried and tested synthetic schemes as well as a selection of recently developed methods describing rationally designed, highly efficient syntheses giving high yield interconversions of functional groups and carbon*b1carbon bond formation under mild, neutral conditions. Written by two experienced practitioners in the field, this volume explodes the myth that free radicals are highly reactive, non-selective intermediates. Contains an extensive introduction discussing principles, advantages, and disadvantages of radical chain reactions Demonstrates functional group interconversions by radical chain reactions Lists carbon*b1carbon bond formations Presents inter- and intramolecular radical chain reactions Includes many examples and experimental details selected by experienced practitioners in this field
Chemists are now moving away from volatile, environmentally harmful, and biologically incompatible organic solvents. With its low cost, ready availability, and capacity to remove environmentally unfriendly by-products, water is an obvious replacement. Recent advances in free radical chemistry in water have expanded the versatility and flexibility of homolytic carbon-hydrogen, carbon-carbon, carbon-halogen, carbon-nitrogen bond formations in aqueous media. This textbook highlights the substantial progress which has been made in the last decade to "tame" the reactive free radical species in aqueous phase reactions. It describes carbon-hydrogen bond formations in aqueous media via radical reactions with a specific focus on HAT (Hydrogen Atom Transfer). Suitable for students of chemistry, industrial chemists and academic researchers, it combines extensive knowledge of free radical chemistry with the latest innovations and creative applications. Divided into five main areas, it covers the: generation of carbon centred free radicals; radical initiators; solubility of substrate; suitability of free radical hydrogen donors, and HAT reactions in aqueous media. The book describes radical reactions in organic and aqueous media and their applications in total synthesis, DNA structural probing, isotope labelling, living polymerization and various other applications. It shows that, armed with an elementary knowledge of kinetics and some common sense, it is possible to harness radicals into tremendously powerful tools for solving synthetic problems. Written with the needs of students in mind, it offers just the right level of detail for undergraduate study. All the basic principles and facts on each topic area are presented in a concise yet comprehensive style that is appropriate for both core and specialist courses. It provides a step-wise introduction, taking students from the basic principles of radical reactions through to their applications in industry and their role in biological and environmental processes. Case studies are used to illustrate reactions in landmark synthesis and problems, with outlined answers, test the reader's understanding. There are also suggestions for further reading.
This book describes the experience over 25 years of the senior author with the chemistry of organic free radicals. It begins with a mechanistic study of industrial importance on the pyrolysis of chlorinated alkanes. It continues with a theory on the biosynthesis of phenolate derived alkaloids involving phenolate radical coupling. There follows 20 years of practical work to prove the theory correct, especially in the case of morphine alkaloids. The book then describes the work on nitrile photolysis (Barton reaction) which involved the invention of new radical chemistry leading to a simple synthesis of the important hormone, aldosterone. There follows a description of the invention of an important new method for the deoxygenation of biologically important molecules, especially sugars and nucleosides, using radical chemistry applied to thiocarbonyl derivatives. Some years later, in a logical extension to carboxylic acids, another new reaction was invented which provides carbon, nitrogen, oxygen and other radicals under mild conditions. A final chapter summarizes recent applications of thiocarbonyl group derived radical reactions by other authors.