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Most syntheses in the chemical research laboratory fail and usually require several attempts before proceeding satisfactorily. Failed syntheses are not only discouraging and frustrating, but also cost a lot of time and money. Many failures may, however, be avoided by understanding the structure-reactivity relationship of organic compounds. This textbook highlights the competing processes and limitations of the most important reactions used in organic synthesis. By allowing chemists to quickly recognize potential problems this book will help to improve their efficiency and success-rate. A must for every graduate student but also for every chemist in industry and academia. Contents: 1 Organic Synthesis: General Remarks 2 Stereoelectronic Effects and Reactivity 3 The Stability of Organic Compounds 4 Aliphatic Nucleophilic Substitutions: Problematic Electrophiles 5 The Alkylation of Carbanions 6 The Alkylation of Heteroatoms 7 The Acylation of Heteroatoms 8 Palladium-Catalyzed C-C Bond Formation 9 Cyclizations 10 Monofunctionalization of Symmetric Difunctional Substrates
Guanidines, amidines and phosphazenes have been attracting attention in organic synthesis due to their potential functionality resulting from their extremely strong basicity. They are also promising catalysts because of their potential for easy molecular modification, possible recyclability, and reduced or zero toxicity. Importantly, these molecules can be derived as natural products – valuable as scientists move towards “sustainable chemistry”, where reagents and catalysts are derived from biomaterial sources. Superbases for Organic Synthesis is an essential guide to these important molecules for preparative organic synthesis. Topics covered include the following aspects: an introduction to organosuperbases physicochemical properties of organic superbases amidines and guanidines in organic synthesis phosphazene: preparation, reaction and catalytic role polymer-supported organosuperbases application of organosuperbases to total synthesis related organocatalysts: proton sponges and urea derivatives amidines and guanidines in natural products and medicines Superbases for Organic Synthesis is a comprehensive, authoritative and up-to-date guide to these important reagents for organic chemists, drug discovery researchers and those interested in the chemistry of natural products.
T. L.S. Kishbaugh: Metalation of Pyrrole.- K.-S. Yeung: Furans and Benzofurans.- P. E. Alford: Lithiation-Based and Magnesation-Based Strategies for the Functionalization of Imidazole: 2001–2010.- L. Fu: Metalation of Oxazoles and Benzoxazoles.- S. Roy • S. Roy • G. W. Gribble: Metalation of Pyrazoles and Indazoles.- J. C. Badenock: Metalation Reactions of Isoxazoles and Benzisoxazoles.- Y.-J. Wu: Thiazoles and Benzothiazoles.- C. F. Nutaitis: Isothiazoles and Benzisothiazoles.- E. R. Biehl: Recent Advances in the Synthesis of Thiophenes and Benzothiophenes.- J. M. Lopchuk: Mesoionics.- J. M. Lopchuk: Azoles with 3-4 Heteroatoms.