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Oxidation plays a crucial role in organic synthesis. This volume presents the array of oxidizing agents and their applications in oxidations. The book describes in great detail a number of reagents of importance. The text includes oxidation of specific types of organic compounds including hydrocarbons, alcohols, phenols, ethers, carbonyl compounds, carboxylic acids, amides, hydrazides, nitro compounds, nitroso compounds, hydroxylamines, azo compounds, azides, hydrazo compounds, amines, phosphorus, arsenic and sulphur compounds. It also covers enzymatic or microbial oxidations as well as oxidations under benign conditions.
Chromium oxidation, well known and widely explored in organic chemistry since the very beginning of this science, is a topic of current interest for the organic chemist as evidenced by the continuous development of new techni ques and procedures reported in the literature. Chromium oxidation is a simple process which can be easily performed in the laboratory and scaled up in industry as well. Although almost every oxidizable organic functional group may undergo chromium oxidation, the most important fields of appli cation are the oxidation of alcohols, allylic and benzylic oxidation, oxidative degradation and oxidation of some organometallic compounds. A high degree of selectivity is often possible by choosing the most suitable reagent among those several ones now available. This book takes account of the various functional groups that undergo oxidation and the entire literature up to 1982. It has been written in the hope to help the synthetic organic chemist in his experimental work. For this purpose a number of tables comprising yields and references have been included; detailed descriptions of typical procedures are meant to show the experimental conditions and the scope of the reactions. We wish to thank Dr. Mario Orena for his valuable scientific and technical assistence and Prof. Bruno Camerino, who read the entire manuscript and corrected many of the errors. Bologna, February 1984 Gianfranco Cainelli Giuliana Cardillo Table of Contents I. Introduction . . . . . . . . . . .
The aim of this book is to help people performing routine operations in Organic Synthesis in a laboratory. This book, the first one in a series, focuses on the oxidation of alcohols to aldehydes and ketones. Probably, this is the most important routine operation in Organic Synthesis.
Electrochemical reactions make significant contributions to organic synthesis either in the laboratory or on an industrial scale. These methods have the potential for developing more "green" chemical synthesis. Over recent years, modern investigations have clarified the mechanisms of important organic electrochemical reactions. Progress has also been made in controlling the reactivity of intermediates through either radical or ionic pathways. Now is the time to gather all the electrochemical work into a textbook.As an essential addition to the armory of synthetic organic chemists, electrochemical reactions give results not easily achieved by many other chemical routes. This book presents a logical development of reactions and mechanisms in organic electrochemistry at a level suited to research scientists and final year graduate students. It forms an excellent starting point from which synthetic organic chemists, in both academia and industry, can appreciate uses for electrochemical methods in their own work. The book is also a reference guide to the literature.
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
C-H, C-O, C-C, and C-Heteroatom bond forming processes by using metal-ligand approaches for the synthesis of organic compounds of biological, pharmacological and organic nanotechnological utility are the key areas addressed in this book. Authored by a European team of leaders in the field, it brings together innovative approaches for a variety of catalysis reactions and processes frequently applied in organic synthesis into a handy reference work. It covers all major types of catalysis, including homogeneous, heterogeneous, and organocatalysis, as well as mechanistic and computational studies. Special attention is paid to the improvements in efficiency and sustainability of important catalytic processes, such as selective oxidations, hydrogenation, and cross-coupling reactions, and to their utilization in industry. The result is a valuable resource for advanced researchers in both academia and industry, as well as graduate students in organic chemistry aiming for chemo-, regio- or stereoselective synthesis of organic compounds by using novel catalytic systems.
As the second volume in a comprehensive encyclopedia of organic reactions, this work provides an elaborated description of the experimental methods used for the oxidation of alcohols to acids. It supplies important data on possible interferences from protecting groups and functional groups, as well as on potential side-reactions. This book is a must for anyone involved in the preparation of organic compounds.
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.
Sets the stage for environmentally friendly industrial organic syntheses From basic principles to new and emerging industrial applications, this book offers comprehensive coverage of heterogeneous liquid-phase selective oxidation catalysis. It fully examines the synthesis, characterization, and application of catalytic materials for environmentally friendly organic syntheses. Readers will find coverage of all the important classes of catalysts, with an emphasis on their stability and reusability. Liquid Phase Oxidation via Heterogeneous Catalysis features contributions from an international team of leading chemists representing both industry and academia. The book begins with a chapter on environmentally benign oxidants and then covers: Selective oxidations catalyzed by TS-1 and other metal-substituted zeolites Selective catalytic oxidation over ordered nanoporous metallo-aluminophosphates Selective oxidations catalyzed by mesoporous metal-silicates Liquid phase oxidation of organic compounds by supported metal-based catalysts Selective liquid phase oxidations in the presence of supported polyoxometalates Selective oxidations catalyzed by supported metal complexes Liquid phase oxidation of organic compounds by metal-organic frameworks Heterogeneous photocatalysis for selective oxidations with molecular oxygen All the chapters dedicated to specific types of catalysts follow a similar organization and structure, making it easy to compare the advantages and disadvantages of different catalysts. The final chapter examines the latest industrial applications, such as the production of catechol and hydroquinone, cyclohexanone oxime, and propylene oxide. With its unique focus on liquid phase heterogeneous oxidation catalysis, this book enables researchers in organic synthesis and oxidation catalysis to explore and develop promising new catalytic materials and synthetic routes for a broad range of industrial applications.
The second edition of Comprehensive Organic Synthesis—winner of the 2015 PROSE Award for Multivolume Reference/Science from the Association of American Publishers—builds upon the highly respected first edition in drawing together the new common themes that underlie the many disparate areas of organic chemistry. These themes support effective and efficient synthetic strategies, thus providing a comprehensive overview of this important discipline. Fully revised and updated, this new set forms an essential reference work for all those seeking information on the solution of synthetic problems, whether they are experienced practitioners or chemists whose major interests lie outside organic synthesis. In addition, synthetic chemists requiring the essential facts in new areas, as well as students completely new to the field, will find Comprehensive Organic Synthesis, Second Edition, Nine Volume Set an invaluable source, providing an authoritative overview of core concepts. Winner of the 2015 PROSE Award for Multivolume Reference/Science from the Association of American Publishers Contains more than170 articles across nine volumes, including detailed analysis of core topics such as bonds, oxidation, and reduction Includes more than10,000 schemes and images Fully revised and updated; important growth areas—including combinatorial chemistry, new technological, industrial, and green chemistry developments—are covered extensively