The Chemistry of Hypervalent Halogen Compounds, 2 Volume Set

The understanding of functional groups is the key to understanding organic chemistry. In the tradition of Patai's Chemistry of Functional Groups each volume treats all aspects of functional groups, touching on theoretical, analytical, synthetic, biological, and industrial aspects. Hypervalent halogen compounds, in particular iodine compounds, are very efficient and selective oxidants which tolerate a wide range of functional groups. The electrophilic properties of these reagents can also be used to introduce other functionalizations. The present volume is the first in the series to survey the properties and chemical behaviour of hypervalent iodine and bromine, their use in organic synthesis, as well as their industrial application. As with all new volumes, the chapters are first published online in Patai's Chemistry of Functional Groups. Once a volume is completed online, it is then published in print format. The printed book offers the traditional quality of the Patai Book Series, complete with an extensive index.Für das Verständnis der organischen Chemie muss man wissen, worum es sich bei funktionalen Gruppen handelt. Dieses Fachbuch steht ganz in der Tradition der Reihe Patai's Chemistry of Functional Groups. Jeder Band deckt sämtliche Aspekte funktionaler Gruppen ab und behandelt dabei theoretische, analytische, synthetische, biologische Aspekte sowie Belange der Industrie. Hypervalente Halogenverbindungen, insbesondere Jodverbindungen, sind überaus effiziente und selektive Oxidantien für eine Vielzahl funktionaler Gruppen. Die elektrophilen Eigenschaften dieser Reagenzien können auch für die Einführung anderer Funktionalisierungen verwendet werden. Dieser Band ist der erste in der Reihe, die die Eigenschaften und das chemische Verhalten von hypervalentem Jod und Brom, deren Einsatz in der organischen Synthese sowie deren industrielle Anwendung untersucht. Wie bei allen neuen Bänden, werden die Kapitel zunächst online in Patai's Chemistry of Functional Groups veröffentlicht. Wenn ein Band online vervollständigt ist, erfolgt die Herausgabe als Printversion. Die Printfassung entspricht der Qualität, die man von der Patai-Reihe kennt, und bietet auch einen umfassenden Index.

1. Fundamental aspects of structure, bonding, and the reactivity of hypervalent iodine compounds 1
Halua Pinto de Magalhães, Oliver Sala, and Hans Peter Lüthi

2. Structural chemistry of hypervalent iodine compounds 31
Michael W. Justik

3. Aspects of the chemical energetics of the hypervalent benzene-based organohalogen halosyl, halyl, and perhalyl species 119
Maja Ponikvar-Svet Joel F. Liebman

4. Mass spectrometry and gas-phase ion chemistry of hypervalent halogen compounds 141
Richard A. J. O’hair

5. NMR of hypervalent iodine compounds 187
Yichen Wu and Alexandr Shafir

6. Synthesis of hypervalent iodine compounds for oxidation reactions 221
Viktor V. Zhdankin

7. Oxidation of alcohols and amines 261
Muhammet Uyanik and Kazuaki Ishihara

8. Oxidative heteroatom–heteroatom bond formation 307
Luis Bering and Andrey P. Antonchick

9. Carbon–heteroatom bond formation mediated by hypervalent iodine 365
Rafael M. Romero and Kilian Muñiz

10. Halogenation and perfluoroalkylation chemistry using hypervalent halogen compounds 409
Dmitry Katayev, Benson Jelier, and Antonio Togni

11. Arylations promoted by hypervalent iodine reagents 461
Piret Villo and Berit Olofsson

12. Alkynylations and vinylations 523
Durga Prasad Hari, Stefano Nicolai, and Jerome Waser

13. Oxidative C−C bond formation (couplings, cyclizations, cyclopropanation, etc.) 581
Toshifumi Dohi and Yasuyuki Kita

14. Rearrangements and fragmentations mediated by hypervalent iodine reagents 665
Sarah E. Wengryniuk, and Sylvain Canesi

15. Industrial applications 707
Tatsuo Kaiho and Viktor V. Zhdankin

16. Hypervalent iodine compounds as precursors for biomedical radiotracers 721
Sanjay Telu, Fabrice G. Siméon, Shuiyu Lu and Victor W. Pike

17. Chemistry of hypervalent bromine 781
Kazunori Miyamoto

18. Stereoselective reactions 807
Fateh V. Singh and ThomasWirth

19. Photochemistry of hypervalent iodine compounds 855
Kunfang Jia and Yiyun Chen

20. Electrochemistry of hypervalent iodine compounds 897
Robert Francke, Timo Broese, and Arend F. Roesel

21. Transition metal-catalyzed reactions with iodine(III) reagents 919
Gergely L. Tolnai, Zsombor Gonda, and Zoltán Novák

Subject index 987

Professor Berit Olofsson, Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden.

Professor Ilan Marek, Department of Chemistry Technion - Israel Institute of Technology, Haifa, Israel.

Professor Zvi Rappoport, Institute of Chemistry The Hebrew University of Jerusalem, Jerusalem, Israel.

PATAI's Chemistry of Functional Groups

The Chemistry of Hypervalent Halogen Compounds

Part 1

A series of advanced treatises founded by Professor Saul Patai and now under the general editorship of Professors Zvi Rappoport, Joel F. Liebman and Ilan Marek

PATAI's Chemistry of Functional Groups publishes comprehensive reviews on all aspects of specific functional groups. Each volume contains outstanding surveys on theoretical and computational aspects, NMR, MS, other spectroscopic methods and analytical chemistry, structural aspects, thermochemistry, photochemistry, synthetic approaches and strategies, synthetic uses and applications in chemical and pharmaceutical industries, and biological, biochemical, and environmental aspects. To date, over 140 volumes, including the update series, have been published in the series.

Recently Published Titles The Chemistry of Organic Silicon Compounds (2 volumes, 4 parts) The Chemistry of Organic Germanium, Tin and Lead Compounds (Volume 2, 2 parts) The Chemistry of Phenols (2 parts) The Chemistry of Organolithium Compounds (2 volumes, 3 parts) The Chemistry of Cyclobutanes (2 parts) The Chemistry of Peroxides (Volume 2, 2 parts) The Chemistry of Organozinc Compounds (2 parts) The Chemistry of Anilines (2 parts) The Chemistry of Organomagnesium Compounds (2 parts) The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids (2 volumes, 4 parts) The Chemistry of Metal Enolates (2 parts) The Chemistry of Organocopper Compounds (2 parts) The Chemistry of Organomanganese Compounds The Chemistry of Organic Selenium and Tellurium Compounds (Volume 3, 2 parts) The Chemistry of Organic Selenium and Tellurium Compounds (Volume 4, 2 parts) The Chemistry of Organoiron Compounds The Chemistry of Peroxides (Volume 3, 2 parts) The Chemistry of Organogold Compounds The Chemistry of Organoaluminum Compounds The Chemistry of Metal Enolates (Volume 2) The Chemistry of Metal Phenolates (Volume 2)

Forthcoming Titles The Chemistry of Nitrogen-rich Functional Groups

PATAI Online

PATAI's Chemistry of Functional Groups is available in electronic format on Wiley Online Library.