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Posted on: May 22, 2007 7:55 PM, by Molecule of the Day
Last November I mentioned the Dess-Martin reagent. Hypervalent iodine reagents are mild oxidants that tend to be more soluble in organic solvent than many of the alternatives. Dess-Martin has largely supplanted another iodine oxidant - IBX acid.
Dess-Martin is more soluble, and, as I understand, a little less inclined to get lively under pressure or impact. Too bad IBX acid is a much cooler name.
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Comments
Hypervalent iodine is so cool!
Posted by: Vince Noir | May 23, 2007 1:39 AM
Unfortunately, using DMP doesn't mean being able to avoid IBX, since IBX is an intermediate to DMP...
Posted by: such.ire | May 24, 2007 2:26 PM
IBX does do some reactions which DMP is not so good at - for example Corey's slective oxidation of diols to lactols - Tet. Lett. 1995, 3485 and Tet. Lett. 1995, 7945, so always worth a careful check!
Wikipedia has a useful introduction (http://en.wikipedia.org/wiki/2-Iodoxybenzoic_acid), which also mentions the theory that preparation by the 'easy' oxone-based route (J. Org. Chem. 1999, 64, 4537) results in non-explosive IBX - a claim not agreed to by the authors of the JOC paper, who found 'an analytically pure sample was subjected to explosability tests, which confirmed the earlier observations by Plumb and Harper.'
Posted by: Steve | May 29, 2007 8:21 AM