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DOI: 10.1055/s-2006-956469
Sodium Periodate (NaIO4) -A Versatile Reagent in Organic Synthesis
Publication History
Publication Date:
08 December 2006 (online)
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Introduction
Sodium periodate (sodium metaperiodate), NaIO4 (mp 300 °C; Figure 1), is commercially available and is applied mainly in aqueous or aqueous-alcoholic solutions. Like the free periodic acid, sodium periodate cleaves vicinal diols to carbonyl compounds. [1] The popularity stems from its specificity, its reactivity under neutral and mild conditions which is compatible with a wide range of functionalities, its stability, and its low cost. [2] Sulfides are transformed by sodium periodate into sulfoxides. It is also a reoxidant of lower-valency ruthenium in oxidations with ruthenium tetroxide. [3]
Figure 1
Tetrabutylammonium periodate, (n-Bu)4NIO4 (mp 175 °C), which is usually prepared in situ from tetrabutylammonium hydrogen sulfate and sodium periodate, [4] is useful in two-phase systems, because it dissolves in chloroform and other organic solvents. [3] It is used in homogeneous oxidations of sulfides, 2-hydroxy acids, and α-bromoketones. [5]
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