Iodanes IBX and Dess-Martin Periodinane

Two of the most important A -iodane reagents are 2-iodoxybenzoic acid (IBX) and Dess-Martin periodinane (DMP). The best current syntheses of the two reagents are as follows, where KHSO5 is potassium hydrogen peroxysulfate  

Acetylation of the 0 /0H group results in DMP being much more soluble in organic solvents than IBX. Both are excellent and selective reagents for oxidation of primary alcohols to aldehydes and secondary alcohols to ketones. Both have a number of advantages over DMSO-based (see Section 6.9) and transition-metal-based protocols. 

Let us first consider the mechanism of oxidation of a primary alcohol by IBX  

Coordination of the alcohol to the pentavalent iodine of IBX is a reasonable starting point  

The alkoxy-2 -iodane intermediate so produced might then be expected to fall apart via a cyclic transition state to a carbonyl compound (an aldehyde in our example) and an aryl-2 -iodane as the final products  

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