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Reactivities, Properties and Structures

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Hypervalent Iodine Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 224))

Abstract

Tri- and pentavalent iodine compounds are called λ3- and λ5-iodanes. Ligand exchange, i.e. displacement of heteroatom ligands of λ3- and λ5-iodanes with external nucleophiles, is a facile low energy process. A very high leaving group ability of λ3-iodanyl groups is among the most important features of λ3-iodanes, which makes it possible to generates highly reactive species such as carbenes, nitrenes, cations, and arynes under mild conditions and to oxidize a wide range of functionalities such as alcohols, amines, sulfides, alkenes, alkynes, and carbonyl compounds. The leaving process is termed reductive elimination, in which the λ3-iodanyl group eliminates with energetically preferable reduction to univalent iodides. The process is also associates with an increase in entropy. Pseudorotation and ligand coupling on iodine(III), and homolytic cleavage of hypervalent iodanes are also discussed. Finally, recent progress in the structural elucidations of λ3-iodanes is shown here.

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima, 770-8505, Japan

    Masahito Ochiai

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  1. Masahito Ochiai
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  1. Department of Chemistry, Cardiff University, CF10 3TB, Cardiff, UK

    Thomas Wirth

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Ochiai, M. (2003). Reactivities, Properties and Structures. In: Wirth, T. (eds) Hypervalent Iodine Chemistry. Topics in Current Chemistry, vol 224. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-46114-0_2

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  • DOI: https://doi.org/10.1007/3-540-46114-0_2

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