Hypervalent Iodine Chemistry


Book Description

Hypervalent Iodine Chemistry is the first comprehensive text covering all of the main aspects of the chemistry of organic and inorganic polyvalent iodine compounds, including applications in chemical research, medicine, and industry. Providing a comprehensive overview of the preparation, properties, and synthetic applications of this important class of reagents, the text is presented in the following way: The introductory chapter provides a historical background and describes the general classification of iodine compounds, nomenclature, hypervalent bonding, structural features, and the principles of reactivity of polyvalent iodine compounds. Chapter 2 gives a detailed description of the preparative methods and structural features of all known classes of organic and inorganic derivatives of polyvalent iodine. Chapter 3, the key chapter of the book, deals with the many applications of hypervalent iodine reagents in organic synthesis. Chapter 4 describes the most recent achievements in hypervalent iodine catalysis. Chapter 5 deals with recyclable polymer-supported and nonpolymeric hypervalent iodine reagents. Chapter 6 covers the "green" reactions of hypervalent iodine reagents under solvent-free conditions or in aqueous solutions. The final chapter provides an overview of the important practical applications of polyvalent iodine compounds in medicine and industry. This book is aimed at all chemists interested in iodine compounds, including academic and industrial researchers in inorganic, organic, physical, medicinal, and biological chemistry. It will be particularly useful to synthetic organic and inorganic chemists, including graduate and advanced undergraduate students. It comprehensively covers the green chemistry aspects of hypervalent iodine chemistry, making it especially useful for industrial chemists.




Hypervalent Iodine Chemistry


Book Description

T. Wirth: Introduction and General Aspects.- M. Ochiai: Reactivities, Properties and Structures.- A. Varvoglis: Preparation of Hypervalent Iodine Compounds.- V.V. Zhdankin: C-C-Bond Forming Reactions.- G.F. Koser: C- Heteroatom-Bond Forming Reactions.- G.F. Koser: Heteroatom- Heteroatom-Bond Forming Reactions.- T. Wirth: Oxidations and Rearrangements.- H. Tohma, Y. Kita: Synthetic Applications (Total Synthesis and Natural Product Synthesis).




Iodine Catalysis in Organic Synthesis


Book Description

Iodine Catalysis in Organic Synthesis The first book of its kind to highlight iodine as a sustainable alternative to conventional transition metal catalysis Iodine Catalysis in Organic Synthesis provides detailed coverage of recent advances in iodine chemistry and catalysis, focusing on the utilization of various iodine-containing compounds as oxidative catalysts. Featuring contributions by an international panel of leading research chemists, this authoritative volume explores the development of environmentally benign organic reactions and summarizes catalytic transformations of molecular iodine and iodine compounds such as hypervalent organoiodine and inorganic iodine salts. Readers are first introduced to the history of iodine chemistry, the conceptual background of homogeneous catalysis, and the benefits of iodine catalysis in comparison with transition metals. Next, chapters organized by reaction type examine enantioselective transformations, catalytic reactions involving iodine, catalyst states, oxidation in iodine and iodine catalyses, and catalytic reactions based on halogen bonding. Practical case studies and real-world examples of different applications in organic synthesis and industry are incorporated throughout the text. An invaluable guide for synthetic chemists in both academic and industrial laboratories, Iodine Catalysis in Organic Synthesis: Provides a thorough overview of typical iodine-catalyzed reactions, catalyst systems, structures, and reactivity Explores promising industrial applications of iodine-based reagents for organic synthesis Highlights the advantages iodine catalysis has over classical metal-catalyzed reactions Discusses sustainable and eco-friendly methods in hypervalent iodine chemistry Edited by two world authorities on the catalytic applications of organoiodine compounds, Iodine Catalysis in Organic Synthesis is required reading for catalytic, organic, and organometallic chemists, medicinal and pharmaceutical chemists, industrial chemists, and academic researchers and advanced students in relevant fields.




Advances in Organic Synthesis


Book Description

"The volume focuses on recent advances in organofluorine chemistry directed towards selective fluorine introduction into various target molecules, employing both traditional and contemporary, electrophilic and nucleophilic, fluorinating agents. It brings t"




Hypervalent Iodine Chemistry


Book Description

The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope of coverage is all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the non-specialist reader, whether in academia or industry, a comprehensive insight into an area where new research is emerging which is of interest to a larger scientific audience. Each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years are presented using selected examples to illustrate the principles discussed. The coverage is not intended to be an exhaustive summary of the field or include large quantities of data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the information presented. Contributions also offer an outlook on potential future developments in the field. Review articles for the individual volumes are invited by the volume editors. Readership: research chemists at universities or in industry, graduate students.




Hypervalent Iodine in Organic Synthesis


Book Description

This book describes the fascinating chemistry of the many kinds of organic compounds of hypervalent iodine. Each chapter deals with a particular iodine compound or families of compounds which have been used as reagents in a plethora of useful transformations. These include assorted oxidation, such as with the precious Dess-Martin reagent as well as with a wide range of further reactions. Prominent features of hypervalent iodine reagents derived from iodobenzene are: ready availability, operational simplicity, mild reaction conditions, and high efficiency. They are environmentally safe and can be recycled. New species may be easily prepared by introducing substituents in the benzene ring or changing the ligand attached to iodine. Their combination with other reagents broadens considerably their synthetic potential. Today, no synthetic chemist can afford to ignore the valuable hypervalentiodine reagents. Features up-to-date coverage of a wide range of topics Includes many tables featuring a diversity of reactivity, and a comprehensive index Acts as a comprehensive, up-to-date reference on all aspects of hypervalent iodine chemistry Contains a section on unusual efficiency of hypervalent iodine reactions




Phenolic Oxidative Coupling


Book Description

Various hypervalent iodine compounds were evaluated as reagents for intramolecular phenolic oxidative coupling. It was found that phenyliodine(III) bis(trifluoroacetate) was effective for the coupling of the monophenolic substrate 13a to 14a under neutral conditions. Vanadium oxytrifluoride and hypervalent iodine compounds were compared as oxidants for the conversion of 32 to 33. In an approach directed at a synthesis of pretazettine (17), phenacylamine 57 was elaborated in two steps to oxazole 50. However, this did not undergo catalytic hydrogenation to the desired oxazolidine 47. Oxazoline 60 proved to be too labile to be isolated upon dehydration of 65, which was prepared from di-octopamine (64) and the acid chloride of piperonylic acid (58). Finally, 64 and piperonal (69) were condensed and treated with ethyl chloroformate to provide trans-2,5-diaryloxazolidine 73. However, the latter was hydrolyzed under coupling conditions. Alternatively, when octopamine and piperonal were condensed and hydrogenated, amine 74 was obtained, which was in turn reacted with 1,1'-carbonyldiimidazole (75) to furnish the 2-oxazolidinone 76. Exposure of 76 to vanadium oxytrifluoride led to 78, which apparently arose from an undesired, spontaneous rear- rangement of the coupling product 77. Attempts to synthesize ether 79 starting with synephrine (81), 2-nitrostyrenes 86, and 4-hydroxymandelates 90 are described. The oxazolidine 97 was prepared from the condensation of synephrine 81 and treated with methyl chioroformate in the presence of methanol to afford acetal 100 in 71% yield. Phenyliodine(III) bis- (trifluoroacetate) was employed to couple 100 to 101 in 5 to 7% yield. Hydrolysis of the urethane moiety of 101 with potassium hydroxide in ethylene glycol gave the amine 105, which underwent a spontaneous cyclization to 107. Formation of the unnatural, cis B-D ring fusion stereochemistry in this ring closure was ascertained by nuclear magnetic resonance spectroscopy.




Chemistry of Hypervalent Compounds


Book Description

Eine umfassende Einführung in das Gebiet der hypervalenten Moleküle und anschauliche Darstellung grundlegender Aufbauprinzipien von Verbindungen der Hauptgruppenelemente und metallorganischen Spezies. Gleichermaßen tiefgründig behandelt werden organische Verbindungen, beispielsweise von Silicium, Phosphor, Schwefel und Iod, und anorganische Moleküle, die unter anderem Antimon, Zinn und Lithium enthalten. (12/98)




Active Oxygen in Chemistry


Book Description

Taking an interdisciplinary approach, this book and its counterpart, Active Oxygen in Biochemistry, explore the active research area of the chemistry and biochemistry of oxygen. Complementary but independent, the two volumes integrate subject areas including medicine, biology, chemistry, engineering, and environmental studies.