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Ynamides contain a triple bond directly connected to a nitrogen atom that bears an electron-withdrawing group. They represent an especially useful and emerging class of reagents, notably because of their strongly polarized triple bond, which enables the development of unique chemical transformations. While they were discovered by Viehe in 1972, their chemistry has remained little investigated and the renaissance of ynamide chemistry started at the dawn of the 20th century with the development of efficient methods for their synthesis. Since then, ynamide chemistry has developed at a remarkably high rate, notably in the past 20 years. Although there are several reviews on ynamide chemistry, most of them are out of date or only focus on special aspects of ynamide chemistry and there is no book about ynamide chemistry yet. Thus, a comprehensive book on ynamide chemistry would be timely and is highly needed. This book covers all aspects of ynamide chemistry, including their discovery, their syntheses, their application in heterocyclic chemistry, natural product synthesis, and organometallic chemistry, and their use as coupling reagents. It provides a systematic and comprehensive overview on ynamide chemistry for the researchers in this field, general readers interested in synthesis, and those who want to enter this field and need a comprehensive and up-to-date overview. Undoubtedly, this book will play a key role in connecting the past with the future to further foster the development of ynamide chemistry.
Modern Synthesis Processes and Reactivity of Fluorinated Compounds focuses on the exceptional character of fluorine and fluorinated compounds. This comprehensive work explores examples taken from all classes of fluorine chemistry and illustrates the extreme reactivity of fluorinating media and the peculiar synthesis routes to fluorinated materials. The book provides advanced and updated information on the latest synthesis routes to fluorocompounds and the involved reaction mechanisms. Special attention is given to the unique reactivity of fluorine and fluorinated media, along with the correlation of those properties to valuable applications of fluorinated compounds. - Contains quality content edited, and contributed, by leading scholars in the field - Presents applied guidance on the preparation of original fluorinated compounds, potentially transferable from the lab scale to industrial applications - Provides practical synthesis information for a wide audience interested in fluorine compounds in many branches of chemistry, materials science, and physics
Providing comprehensive insight into the use of copper in cross-coupling reactions, Copper-Mediated Cross-Coupling Reactions provides a complete up-to-date collection of the available reactions and catalytic systems for the formation of carbon-heteroatom and carbon-carbon bonds. This essential reference covers a broad scope of copper-mediated reactions, their variations, key advances, improvements, and an array of academic and industrial applications that have revolutionized the field of organic synthesis. The text also discusses the mechanism of these transformations, the use of copper as cost-efficient alternative to palladium, as well as recently developed methods for conducting copper-mediated reactions with supported catalysts.
Sulfonyl ynamides are highly versatile and synthetically useful reagents. This thesis details the modular synthesis and use of sulfonyl ynamides in order to access N-heterocyclic scaffolds, such as quinolines and pyrazoles. The synthesis of a wide array of sulfonyl ynamides can be realized via copper-catalyzed amidative cross-couplings or by elimination of dichloroenamide precursors. Additionally the use of Sonogashira chemistry to further diversify terminal ynamides and the synthesis of solid-supported ynamides was investigated. Electrophilically-activated amides can be reacted with sulfonyl ynamides in order to access highly functionalized 4-aminoquinolines. The straightforward amide activation procedure with triflic anhydride and 2-chloropyridine was found to tolerate a wide range of substrates, which allowed for the development of a library of 4-aminoquinolines with ease. Moreover, 4-aminopyrazoles can be prepared by reacting terminal sulfonyl ynamides with sydnones under copper catalysis. However, as the copper catalysts were also found to promote the degradation of the ynamides, a copper-free strain-promoted alternative was developed. An in situ prepared 3-azacyclohexyne was found to tolerate a wide array of C-4 substituted sydnones, producing a mixture of both the 3,4- and 4,3-fused pyrazoles in good yields. Additional investigations into heterocyclic methodology led to the development of highly sophisticated, non-symmetrical and axially-chiral dibenzo-1,3-diazepines, -oxazepines and -thiazepines from simple, commercially available anilines. The anilines were coupled to their corresponding reaction partners via a chloromethyl intermediate and the 7-membered ring was subsequently formed using direct arylation.
Advances in Organic Synthesis is a book series devoted to the latest advances in synthetic approaches towards challenging structures. The series presents comprehensive reviews written by eminent authorities on different synthetic approaches to selected target molecules and new methods developed to achieve specific synthetic transformations or optimal product yields. Advances in Organic Synthesis is essential for all organic chemists in academia and the industry who wish to keep abreast of rapid and important developments in the field. This volume presents the following reviews: Electroluminescent polymers - a review on synthesis from organic compounds Remarkable advances in the asymmetric synthesis of biologically active natural compounds from the advent of chiral auxiliaries The chemistry of ynamides and their application in organic synthesis Carbon-heteroatom bond formation for medium ring heterocycles Tin(ii) salts: versatile and efficient lewis acid catalysts in reactions to add value to the glycerol and terpenic alcohols (E)-n-methyl-1-(methylthio)-2-nitroethenamine (nmsm) as a versatile ambiphilic synthon in organic synthesis.
Dipolar cycloaddition reactions have found many useful applications in chemistry, particularly with respect to the synthesis of compounds with new chiral centers. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products updates the popular 1984 edition, featuring the advances made over the past twenty years and focusing on synthetic applications.
A practical handbook for chemists performing bond forming reactions, this book features useful information on the synthesis of common functional groups in organic chemistry. • Details modern functional group synthesis through carbon-heteroelement (N, O, P, S, B, halogen) bond forming reactions with a focus on operational simplicity and sustainability. • Summarizes key and recent developments – which are otherwise scattered across journal literature – into a single source • Contains over 100 detailed preparations of common functional groups • Included 25 troubleshooting guides with suggestions and potential solutions to common problems. • Complements the text in enhanced ebook editions with tutorial videos where the author provides an introduction to microwave assisted chemistry
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.
Continuing the tradition of providing significant and interesting procedures, Organic Syntheses, Collective Volume XII is a compilation of revised editions of Annual Volumes 85 through 89. The contents of this volume are organized by primarily by reaction type, with the precise classification made according to the bias of the editor, who attempted to ascertain the primary purpose or utility of the procedure.