Side Reactions In Organic Synthesis

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

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.

This English edition of a best-selling and award-winning German textbook Reaction Mechanisms: Organic Reactions · Stereochemistry · Modern Synthetic Methods is aimed at those who desire to learn organic chemistry through an approach that is facile to understand and easily committed to memory. Michael Harmata, Norman Rabjohn Distinguished Professor of Organic Chemistry (University of Missouri) surveyed the accuracy of the translation, made certain contributions, and above all adapted its rationalizations to those prevalent in the organic chemistry community in the English-speaking world. Throughout the book fundamental and advanced reaction mechanisms are presented with meticulous precision. The systematic use of red "electron-pushing arrows" allows students to follow each transformation elementary step by elementary step. Mechanisms are not only presented in the traditional contexts of rate laws and substituent effects but, whenever possible, are illustrated using practical, useful and state-of-the-art reactions. The abundance of stereoselective reactions included in the treatise makes the reader familiar with key concepts of stereochemistry. The fundamental topics of the book address the needs of upper-level undergraduate students, while its advanced sections are intended for graduate-level audiences. Accordingly, this book is an essential learning tool for students and a unique addition to the reference desk of practicing organic chemists, who as life-long learners desire to keep abreast of both fundamental and applied aspects of our science. In addition, it will well serve ambitious students in chemistry-related fields such as biochemistry, medicinal chemistry and pharmaceutical chemistry. From the reviews: "Professor Bruckner has further refined his already masterful synthetic organic chemistry classic; the additions are seamless and the text retains the magnificent clarity, rigour and precision which were the hallmark of previous editions. The strength of the book stems from Professor Bruckner’s ability to provide lucid explanations based on a deep understanding of physical organic chemistry and to limit discussion to very carefully selected reaction classes illuminated by exquisitely pertinent examples, often from the recent literature. The panoply of organic synthesis is analysed and dissected according to fundamental structural, orbital, kinetic and thermodynamic principles with an effortless coherence that yields great insight and never over-simplifies. The perfect source text for advanced Undergraduate and Masters/PhD students who want to understand, in depth, the art of synthesis ." Alan C. Spivey, Imperial College London "Bruckner’s ‘Organic Mechanisms’ accurately reflects the way practicing organic chemists think and speak about organic reactions. The figures are beautifully drawn and show the way organic chemists graphically depict reactions. It uses a combination of basic valence bond pictures with more sophisticated molecular orbital treatments. It handles mechanisms both from the "electron pushing perspective" and from a kinetic and energetic view. The book will be very useful to new US graduate students and will help bring them to the level of sophistication needed to be serious researchers in organic chemistry." Charles P. Casey, University of Wisconsin-Madison "This is an excellent advanced organic chemistry textbook that provides a key resource for students and teachers alike." Mark Rizzacasa, University of Melbourne, Australia.

This volume is a compilation of the most commonly used and widely known name reactions and reagents in modern synthetic organic chemistry. Each item is listed alphabetically, giving structure, physical properties, major uses, preparation, commercial availability and secondary information.

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

From Boron Trifluoride to Zinc, the 52 most widely used reagents in organic synthesis are described in this unique desktop reference for every organic chemist. The list of reagents contains classics such as N-Bromosuccinimide (NBS) and Trifluoromethanesulfonic Acid side by side with recently developed ones like Pinacolborane and Tetra-n-propylammonium Perruthenate (TPAP). For each reagent, a concise article provides a brief description of all important reactions for which the reagent is being used, including yields and reaction conditions, an overview of the physical properties of the reagent, its storage conditions, safe handling, laboratory synthesis and purification methods. Advantages and disadvantages of the reagent compared to alternative synthesis methods are also discussed. Reagents have been hand-picked from among the 5000 reagents contained in EROS, the Encyclopedia of Reagents for Organic Synthesis. Every organic chemist should be familiar with these key reagents that can make almost every reaction work.

70 Jahre Forschung an der Diels-Alder-Reaktion: Dieses Buch fasst die wichtigsten und beeindruckendsten Ergebnisse in einzigartiger Weise zusammen! Zunächst werden die Grundprinzipien der Reaktion klar und verständlich anhand übersichtlicher Graphiken erläutert. Spezielle Vorschriften und gegebenenfalls ihre industrielle Umsetzung werden anschließend erklärt. Einen Schwerpunkt bilden auch physikalische und katalytische Verfahren zur Steigerung der Selektivität der Reaktion. Cycloadditionen in konventionellen und unkonventionellen Medien werden vorgestellt. Mit über 1.000 Literaturverweisen!