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The Chemistry of Hypervalent Halogen Compounds




The Chemistry of Hypervalent Halogen Compounds

Berit Olofsson, Ilan Marek, Zvi Rappoport

ISBN: 978-1-119-35230-3 April 2019 1032 Pages


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.

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