O-Iodylbenzoic acid

The closely related o-iodylbenzoic acid (IBX) and Dess-Martin oxidations have proved to be effective methods for the synthesis of peptide aldehydes (Table 7, Scheme 6) 9 38 39] 2-Iodobenzoic acid is oxidized by potassium bromate to form 2-iodylbenzoic acid (IBX), which can be used directly for IBX oxidation. IBX can be further treated with acetic anhydride and TosOH at 100 °C for 40 minutes to form the more stable Dess-Martin periodinane reagent 45 46]... 

The Dess-Martin reagent was prepared in two steps from o-iodobenzoic acid which was first converted into the isolable o-iodylbenzoic acid , of cyclic structure. The original procedure for the second step was substantially improved. 

HAZARD the intermediate o-iodylbenzoic acid is explosive on heating above 200°C and also upon impact the Dess-Martin reagent explodes violently on heating under confinement, at 130°C. 

The mono-acetylated form of the above o-iodylbenzoic acid, i.e. l-acetoxy-1,2-benziodoxol-3( 1 //)-one-1 -oxide, is probably the actual oxidizing species [28],... 

REACTIONS WITH DESS-MARTIN REAGENT AND o-IODYLBENZOIC ACID... 

Reagents of Iodine)V Reactions with Iodylarenes. Reactions with Dess-Martin Reagent and o-iodylbenzoic Acid. 

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