Hypervalent iodine reagents reactivity patterns

The oxidation of phenols with hypervalent iodine compounds has been used frequently and nucleophilic additions can be performed as well as cyclization reactions using this technique. The resulting quinone derivatives show high reactivity and they have been used in a various subsequent reactions. Substituted phenols like 32 [78] or 34 [79] have been oxidized by hypervalent iodine reagents and, depending on the substitution pattern, cyclizations have taken place as shown in Scheme 16. Product 33 is unstable and undergoes subsequent... 

The reactivity pattern of recyclable hypervalent iodine reagents 65-67,69-71,73,74 and 76 is similar to the common iodobenzene-based reagents [34], For example, the recyclable (diacetoxyiodo)arenes 65,69,73 and 76 can be used instead of (diacetoxyiodo)benzene in the KBr or TEMPO-catalyzed oxidations of alcohols [74-78], while [hydroxy(tosyloxy)iodo]arenes 67, 71 and 74 are excellent reagents for tosyloxylation of ketones (Scheme 5.28) [76]. 

The reactivity pattern of compounds 90 and 91 is similar to common hypervalent iodine reagents, as illustrated by their use for the oxidation of sulfides, oxidative iodination of arenes and a-tosyloxylation of ketones (Scheme 5.32) [89]. The products of all these reactions can be conveniently separated from the by-product, 3-iodobenzoic acid, by simple treatment with ion-exchange resin IRA-900 according to... 

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