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Side Reactions in Organic Synthesis

Side Reactions in Organic Synthesis
Author: Florencio Zaragoza Dörwald
Publisher: John Wiley & Sons
Total Pages: 389
Release: 2006-03-06
Genre: Science
ISBN: 3527604987

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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


Side Reactions in Organic Synthesis

Side Reactions in Organic Synthesis
Author: Florencio Zaragoza Dörwald
Publisher: Wiley-VCH
Total Pages: 389
Release: 2004-12-27
Genre: Science
ISBN: 9783527310210

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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


Side Reactions in Organic Synthesis II

Side Reactions in Organic Synthesis II
Author: Florencio Zaragoza Dörwald
Publisher: John Wiley & Sons
Total Pages: 417
Release: 2014-06-23
Genre: Science
ISBN: 3527681728

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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!


Side Reactions in Peptide Synthesis

Side Reactions in Peptide Synthesis
Author: Yi Yang
Publisher: Academic Press
Total Pages: 378
Release: 2015-09-01
Genre: Science
ISBN: 0128011815

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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


Named Organic Reactions

Named Organic Reactions
Author: Thomas Laue
Publisher: John Wiley & Sons
Total Pages: 320
Release: 2005-08-19
Genre: Science
ISBN: 0470026448

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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.


Introduction to Strategies for Organic Synthesis

Introduction to Strategies for Organic Synthesis
Author: Laurie S. Starkey
Publisher: John Wiley & Sons
Total Pages: 360
Release: 2012-01-18
Genre: Science
ISBN: 1118180852

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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.


Strategic Applications of Named Reactions in Organic Synthesis

Strategic Applications of Named Reactions in Organic Synthesis
Author: Laszlo Kurti
Publisher: Elsevier
Total Pages: 808
Release: 2005-04-29
Genre: Science
ISBN: 0080575412

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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


Organic Synthesis

Organic Synthesis
Author: Michael Smith
Publisher: Academic Press
Total Pages: 1108
Release: 2016-11-22
Genre: Science
ISBN: 0128008075

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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


Organic Mechanisms

Organic Mechanisms
Author: Reinhard Bruckner
Publisher: Springer Science & Business Media
Total Pages: 873
Release: 2010-01-20
Genre: Science
ISBN: 3642036503

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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.


Essential Reagents for Organic Synthesis

Essential Reagents for Organic Synthesis
Author: Philip L. Fuchs
Publisher: John Wiley & Sons
Total Pages: 640
Release: 2016-07-19
Genre: Science
ISBN: 1119279879

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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.