IBX, 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (2iodoxybenzoic acid 1), has been known for more than a century, although its presence on the scene of organic synthesis has remained limited primarily due to its remarkable insolubility in most organic solvents. 1,2b,3a
The ultracentennial 10-1-4 iodinane oxide IBX (3; o-iodoxybenzoic acid; 1-hydroxy-1,2-benziodoxol-3(lif)-one 1-oxide) represents a new oxidizing reagent that successfully joins to the large family of known oxidants. IBX, in contrast to other valuable oxidants, is inexpensive to prepare and easy to handle, can tolerate moisture and water, and generally gives very good yields. Furthermore, IBX is mild and chemoselective (primary alcohols are converted into aldehydes with no overoxidation to acids; 1,2-diols are converted to -ketols or a-diketones without oxidative cleavage; amino alcohols are oxidized to amino carbonyls, without protection of the amino group; sensitive heterocycles are not affected; various other functional groups are compatible with IBX oxidation). IBX is versatile (it works in various solvents and it is highly sensitive to temperature variations), and its solutions in DMSO are stable enough to carry out the oxidation reaction easily.
The title reaction with the mild and chemoselective reagent IBX is reported for a variety of alcohols like (I), (VII), (XI). -(FRIGERIO, M.; SANTAGOSTINO, M.; SPUTORE, S.; PALMISANO, G.; J.
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