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
Side Reactions in Peptide Synthesis, based on the author's academic and industrial experience, and backed by a thorough review of the current literature, provides analysis of, and proposes solutions to, the most frequently encountered side reactions during peptide and peptidomimetic synthesis. This valuable handbook is ideal for research and process chemists working with peptide synthesis in diverse settings across academic, biotech, and pharmaceutical research and development. While peptide chemistry is increasingly prevalent, common side reactions and their causes are often poorly understood or anticipated, causing unnecessary waste of materials and delay. Each chapter discusses common side reactions through detailed chemical equations, proposed mechanisms (if any), theoretical background, and finally, a variety of possible solutions to avoid or alleviate the specified side reaction. - Provides a systematic examination on how to troubleshoot and minimize the most frequent side reactions in peptide synthesis - Gives chemists the background information and the practical tools they need to successfully troubleshoot and improve results - Includes optimization-oriented analysis of side reactions in peptide synthesis for improved industrial process development in peptidyl API (active pharmaceutical ingredient) production - Answers the growing, global need for improved, replicable processes to avoid impurities and maintain the integrity of the end product. - Presents a thorough discussion of critical factors in peptide synthesis which are often neglected or underestimated by chemists - Covers solid phase and solution phase methodologies, and provides abundant references for further exploration
This new textbook is the successor to the volume "Side Reactions in Organic Synthesis - A Guide to Successful Synthesis Design" (2004), written by the same author. Whereas the predecessor mainly covered the limitations of aliphatic substitution reactions, this new volume focuses on the most important aromatic substitution reactions, both electrophilic and nucleophilic, such as amination reactions, halogenation reactions, Friedel-Crafts acylations, or transition metal-catalyzed arylation reactions. Each chapter not only describes the scope of a specific reaction type, but also reveals what cannot be achieved with this reaction, i.e. what type of side reactions are to be expected with certain starting materials or electrophiles/nucleophiles. With its unique approach, this is a must-have book for graduate students in organic chemistry and synthetic chemists both in academia and industry!
This Second edition contains consise information on 134 carefully chosen named organic reactions - the standard set of undergraduate and graduate synthetic organic chemistry courses. Each reaction is detailed with clearly drawn mechanisms, references from the primary literature, and well-written accounts covering the mechanical aspects of the reactions, and the details of side reactions and substrate limitations. For the 2nd edition the complete text has been revised and updated, and four new reactions have been added: Baylis-Hillmann Reaction, Sonogashira Reaction, Pummerer Reaction, and the Swern Oxidation und Cyclopropanation. An essential text for students preparing for exams in organic chemistry.
Organic Synthesis, Fourth Edition, provides a reaction-based approach to this important branch of organic chemistry. Updated and accessible, this eagerly-awaited revision offers a comprehensive foundation for graduate students coming from disparate backgrounds and knowledge levels, to provide them with critical working knowledge of basic reactions, stereochemistry and conformational principles. This reliable resource uniquely incorporates molecular modeling content, problems, and visualizations, and includes reaction examples and homework problems drawn from the latest in the current literature. In the Fourth Edition, the organization of the book has been improved to better serve students and professors and accommodate important updates in the field. The first chapter reviews basic retrosynthesis, conformations and stereochemistry. The next three chapters provide an introduction to and a review of functional group exchange reactions; these are followed by chapters reviewing protecting groups, oxidation and reduction reactions and reagents, hydroboration, selectivity in reactions. A separate chapter discusses strategies of organic synthesis, and he book then delves deeper in teaching the reactions required to actually complete a synthesis. Carbon-carbon bond formation reactions using both nucleophilic carbon reactions are presented, and then electrophilic carbon reactions, followed by pericyclic reactions and radical and carbene reactions. The important organometallic reactions have been consolidated into a single chapter. Finally, the chapter on combinatorial chemistry has been removed from the strategies chapter and placed in a separate chapter, along with valuable and forward-looking content on green organic chemistry, process chemistry and continuous flow chemistry. Throughout the text, Organic Synthesis, Fourth Edition utilizes Spartan-generated molecular models, class tested content, and useful pedagogical features to aid student study and retention, including Chapter Review Questions, and Homework Problems. A full Solutions Manual is also available online for qualified instructors, to support teaching. - Winner, 2018 Textbook Excellence Award (Texty) from the Textbook and Academic Authors Association - Fully revised and updated throughout, and organized into 19 chapters for a more cogent and versatile presentation of concepts - Includes reaction examples taken from literature research reported between 2010-2015 - Features new full-color art and new chapter content on process chemistry and green organic chemistry - Offers valuable study and teaching tools, including Chapter Review Questions and Homework Problems for students; Solutions Manual for qualified course instructors
The stepping-stone text for students with a preliminary knowledge of organic chemistry looking to move into organic synthesis research and graduate-level coursework Organic synthesis is an advanced but important field of organic chemistry, however resources for advanced undergraduates and graduate students moving from introductory organic chemistry courses to organic synthesis research are scarce. Introduction to Strategies for Organic Synthesis is designed to fill this void, teaching practical skills for making logical retrosynthetic disconnections, while reviewing basic organic transformations, reactions, and reactivities. Divided into seven parts that include sections on Retrosynthesis and Protective Groups; Overview of Organic Transformations; Synthesis of Monofunctional Target Molecules; Synthesis of Target Molecules with Two Functional Groups; Synthesis of Aromatic Target Molecules; Synthesis of Compounds Containing Rings; and Predicting and Controlling Stereochemistry, the book covers everything students need to successfully perform retrosynthetic analyses of target molecule synthesis. Starting with a review of functional group transformations, reagents, and reaction mechanisms, the book demonstrates how to plan a synthesis, explaining functional group analysis and strategic disconnections. Incorporating a review of the organic reactions covered, it also demonstrates each reaction from a synthetic chemist's point of view, to provide students with a clearer understanding of how retrosynthetic disconnections are made. Including detailed solutions to over 300 problems, worked-through examples and end-of-chapter comprehension problems, Introduction to Strategies for Organic Synthesis serves as a stepping stone for students with an introductory knowledge of organic chemistry looking to progress to more advanced synthetic concepts and methodologies.
Kurti and Czako have produced an indispensable tool for specialists and non-specialists in organic chemistry. This innovative reference work includes 250 organic reactions and their strategic use in the synthesis of complex natural and unnatural products. Reactions are thoroughly discussed in a convenient, two-page layout--using full color. Its comprehensive coverage, superb organization, quality of presentation, and wealth of references, make this a necessity for every organic chemist. - The first reference work on named reactions to present colored schemes for easier understanding - 250 frequently used named reactions are presented in a convenient two-page layout with numerous examples - An opening list of abbreviations includes both structures and chemical names - Contains more than 10,000 references grouped by seminal papers, reviews, modifications, and theoretical works - Appendices list reactions in order of discovery, group by contemporary usage, and provide additional study tools - Extensive index quickly locates information using words found in text and drawings
Domino reactions enable you to build complex structures in one-pot reactions without the need to isolate intermediates- a dream comes true. In this book, the well-respected expert, Professor Lutz Tietze, summarizes the possibilities of this reaction type - an approach for an efficiant, economically benificial and ecological benign synthesis. A definite must for every organic chemist.
Organic Synthesis: Today and Tomorrow covers the proceedings of the Third International Union of Pure and Applied Chemistry (IUPAC) Symposium on Organic Synthesis. The book covers topics that tackle relevant issues about organic chemistry. Comprised of 27 chapters, the book covers lectures that tackle topics pertaining organic chemistry. These topics include useful synthetic methods for general application; development of chemistry concepts for use in construction of molecular sub-assemblies; and interplay of synthetic methodology and the total synthesis of organic compounds. The book will be of great interest to scientists, such as biochemists who are concerned with the advances in organic chemistry.
Current Trends in Organic Synthesis is a collection of papers presented at the Fourth International Conference on Organic Synthesis, held in Tokyo, Japan on August 22-27, 1982. This conference brings together the significant achievements in the diversified frontier fields of organic synthesis. This book is composed of 33 chapters. The first chapters focus on the synthesis of biologically active natural compounds, including metabolites of arachidonic acid, erythromycin A, verrucarins, steroids, anthracyclines, terpenes, yeast alanine t-RNA, beta-lactam antibiotics, and palitoxin. Other chapters deal with the central problems in stereoselective and chiral synthesis, as well as processes of high degree of stereochemical control and asymmetric induction. These chapters also describe chiral pool synthesis by means of carbohydrate precursors. This book also examines the methodologies in organic synthesis using reagents with boron, aluminum, transition metals, silicon, phosphorus, and sulfur. The remaining chapters are devoted to reactions involving radical initiated ring closure, small ring hydrogenolysis, annulene synthesis, vicarious nucleophilic substitution of aromatic hydrogen, and dichlorine monoxide mediated powerful chlorination. This book is of value to organic chemists and allied scientists.
