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Organic Chemistry: Structure, Mechanism, Synthesis, Second Edition, provides basic principles of this fascinating and challenging science, which lies at the interface of physical and biological sciences. Offering accessible language and engaging examples and illustrations, this valuable introduction for the in-depth chemistry course engages students and gives future and new scientists a new approach to understanding, rather than merely memorizing the key concepts underpinning this fundamental area. The book builds in a logical way from chemical bonding to resulting molecular structures, to the corresponding physical, chemical and biological properties of those molecules. The book explores how molecular structure determines reaction mechanisms, from the smallest to the largest molecules—which in turn determine strategies for organic synthesis. The book then describes the synthetic principles which extend to every aspect of synthesis, from drug design to the methods cells employ to synthesize the molecules of which they are made. These relationships form a continuous narrative throughout the book, in which principles logically evolve from one to the next, from the simplest to the most complex examples, with abundant connections between the theory and applications. Featuring in-book solutions and instructor PowerPoint slides, this Second Edition offers an updated and improved option for students in the two-semester course and for scientists who require a high quality introduction or refresher in the subject. - Offers improvements for the two-semester course sequence and valuable updates including two new chapters on lipids and nucleic acids - Features biochemistry and biological examples highlighted throughout the book, making the information relevant and engaging to readers of all backgrounds and interests - Includes a valuable and highly-praised chapter on organometallic chemistry not found in other standard references
Stereoselective Synthesis of Tetrasubstituted Alkenes via Torquoselectivity-Controlled Olefination of Carbonyl Compounds with Ynolates, by Mitsuru Shindo and Kenji Matsumoto.- Stereoselective Synthesis of Z-Alkenes, by Woon-Yew Siau, Yao Zhang and Yu Zhao.- Stereoselective Synthesis of Mono-fluoroalkenes, by Shoji Hara.- Recent Advances in Stereoselective Synthesis of 1,3-Dienes, by Michael De Paolis, Isabelle Chataigner and Jacques Maddaluno.- Selective Olefination of Carbonyl Compounds via Metal-Catalyzed Carbene Transfer from Diazo Reagents, by Yang Hu and X. Peter Zhang.- Selective Alkene Metathesis in the Total Synthesis of Complex Natural Product, by Xiaoguang Lei and Houhua Li.- Olefination Reactions of Phosphorus-Stabilized Carbon Nucleophiles, by Yonghong Gu and Shi-Kai Tian.- Alkene Synthesis Through Transition Metal-Catalyzed Cross-Coupling of N-Tosylhydrazones, by Yan Zhang and Jianbo Wang.
Volume 4 focuses on additions and the resulting substitutions at carbon-carbon &pgr;-bonds. Part 1 includes processes generally considered as simple polar reactions, reactive electrophiles and nucleophiles adding to alkenes and alkynes. A major topic is Michael-type addition to electron deficient &pgr;-bonds, featured in the first six chapters. In part 2 are collected the four general processes leading to nucleophilic aromatic substitution, including radical chain processes and transition metal activation through to &pgr;-complexation. Metal-activated addition (generally by nucleophiles) to alkenes and polyenes is presented in part 3, including allylic alkylation catalyzed by palladium. The coverage of nonpolar additions in part 4 includes radical additions, organometal addition (Heck reaction), carbene addition, and 1,3-dipolar cycloadditions.
This thesis deals with the Ti(III) catalyzed synthesis of exocyclic allenes and the development of new titanocene complexes. It is structured in six chapters: Chapter 1 is a general introduction about the generation and reactivity of [TiCp2Cl]. A review about the different [TiCp2Cl] catalyzed or promoted reactions reported to date, is included. Chapter 2 is divided in introduction and results and discussion. In the introduction, an overview about the promoted or catalyzed methodologies, already available for the synthesis of α-allenols, is included. Results and discussion section is sub-divided in other two parts. The first one describes the synthesis of carbocyclic or nitrogen heterocyclic precursors bearing a propargyl halide and a carbonyl group. Next, the [TiCp2Cl] catalyzed synthesis of exocyclic allenols is studied. Additionally, a mechanistic study through deuterium incorporation and reaction of secondary propargyl halide precursors is performed. In the second part, the preparation of oxygen precursors and its cyclization are studied. In chapter 3, there is an introduction about enantioselective syntheses using chiral titanocene catalysts. The results and discussion section deals with the enantioselective cyclization of some of the precursors previously prepared using precatalyst (R,R)-ethylenebis(4,5,6,7-tetrahydro-1-indenyl) titanium(IV), also known as Brintzinger complex. A formal synthesis of the alkaloid (})-stemoamide is carried out in chapter 4, being the key step for this synthesis the generation of an α-allenol derivative through a [TiCp2Cl] catalyzedcyclization. This chapter is also divided in an introduction, in which a review about the different methods of synthesis of stemoamide are included, and results and discussion. Chapter 5 compiles the project that I have developed during my research stay at University of Bonn, under the supervision of Prof. Gansauer. The target of this project was to develop an azide functionalized short linker titanocene derivative with the aim of linking it to a surface by click chemistry. The chapter is divided in introduction and results and discussion. In the introduction the different methodologies for the synthesis of titanocene derivatives are reviewed. This section also includes the background in which this project is based. Chapter 6 includes the experimental part. In this chapter all reactions performed during the development of this thesis, as well as the spectroscopic characterization of compounds, are compiled.
There is a vast and often bewildering array of synthetic methods and reagents available to organic chemists today. The Best Synthetic Methods series allows any scientist who is interested in the chemical transformations of molecules to choose between all the alternatives and assess their real advantages and limitations. With the emphasis on laboratory use, these volumes represent a comprehensive and practical guide to modern synthetic organic chemistry. Best Synthetic Methods: Acetylenes, Allenes and Cumulenes is the product of the author's many years practical experience and reading of the original literature. It contains a valuable distillation and critical evaluation of the Best Synthetic Methods for the formation and reaction of molecules containing carbon-carbon triple bonds or cumulative carbon-carbon double bonds. A brief review of each area is provided, but the emphasis in all cases is on describing efficient practical methods to effect the transformations described. The reader can therefore use this book to rapidly review and select the best methods of performing a synthetic conversion to create or modify a molecule containing an acetylene, allene or cumulene functionality. In addition, the documentation of a large number of experimental recipes enables the user to synthesise an unsaturated molecule without the need to access to the original literature. - Reviews and evaluates the various methods for the formation and reaction of acetylenes, cumulenes and allenes - Provides detailed practical experimental for many important reactions - General tips and analytical data are provided from the author's own extensive research in this area
Volume 8.
The Organic Chemistry of Nickel, Volume I: Organonickel Complexes is devoted to a description of the organonickel complexes. The major goal is to provide a reference work, and for this reason a conventional layout has been adopted with separate chapters devoted to each type of organic ligand. In the interest of readability, known compounds have been assembled in tables at the end of each chapter, thereby allowing the text to be used for discussions of the general chemistry involved and to highlight the special reactions associated with nickel. Conscious of the needs of organometallic chemists, the authors included systems in which no nickel-carbon bond is involved. Among these is a chapter on the tetrakisligand nickel complexes and sections on dioxygen and azobenzene complexes. The nitrosyl complexes and complexes containing a metal-metal bond—topics frequently considered to be part of the domain of the organometallic chemist—have not received individual attention. Tables of the observed bond distances in organonickel complexes are provided as an Appendix; a short list of the more important review articles relevant to each organic ligand can be found at the end of each chapter.
This series offers practical help for advanced undergraduate, graduate and postgraduate students, as well as experienced chemists in industry and academia working with catalysts in organic and organometallic synthesis. It features tested and validated procedures, authoritative reviews on classes of catalysts, and assessments of all types of catalysts. Micro- and Mesoporous Solid Catalysts describes the use of zeolites and mesoporous solids as catalysts for the production of fine and specialty chemicals. Specific tips and hints are provided and some typical procedures are described in detail In addition to discussing the pros and cons, several major organic transformations are examined including aromatic substitutions, heterocyclic ring formation, amines synthesis, oligomerisation, oxidation and hydroxylation, and other regioselective and stereoselective reactions Features tutorial introductory chapters, including tips and hints for achieving successful organic transformations Important reactions are featured together with recommendations to resolve potential problems.
Class-tested and thoughtfully designed for student engagement, Principles of Organic Chemistry provides the tools and foundations needed by students in a short course or one-semester class on the subject. This book does not dilute the material or rely on rote memorization. Rather, it focuses on the underlying principles in order to make accessible the science that underpins so much of our day-to-day lives, as well as present further study and practice in medical and scientific fields. This book provides context and structure for learning the fundamental principles of organic chemistry, enabling the reader to proceed from simple to complex examples in a systematic and logical way. Utilizing clear and consistently colored figures, Principles of Organic Chemistry begins by exploring the step-by-step processes (or mechanisms) by which reactions occur to create molecular structures. It then describes some of the many ways these reactions make new compounds, examined by functional groups and corresponding common reaction mechanisms. Throughout, this book includes biochemical and pharmaceutical examples with varying degrees of difficulty, with worked answers and without, as well as advanced topics in later chapters for optional coverage. Incorporates valuable and engaging applications of the content to biological and industrial uses Includes a wealth of useful figures and problems to support reader comprehension and study Provides a high quality chapter on stereochemistry as well as advanced topics such as synthetic polymers and spectroscopy for class customization