A Short Review on DMP

Laundry! Some laundry and a LEADING QUESTION.

 
In their 1983 article titled, Readily Accessible 12-I-5 Oxidant for Conversion of Primary and Secondary Alcohols to Aldehydes and Ketones2, Dess and Martin describe their newfound hypervalent iodine reagent. This reagent is a mild, versatile reagent for selective oxidation of primary and secondary alcohols to aldehydes and ketones, hydoxamic acids to acyl notroso compounds, deprotection of thioacetals and deoximation of ketoximes to ketones. This reaction avoids some of the difficulties found in other methods for oxidation of alcohols, like long reaction times, difficult workup procedures, or the need to use a large excess of the oxidizing agent. In addition, DMP is less toxic when compared with other oxidizing reagents, like chromium. The reagent is sparingly soluble in hexane or ether but is very soluble in chloroform, methylene chloride, or acetonitrile. Periodinane has an indefinite shelf life in a sealed container. DMP is readily available. Sigma-Aldrich sells 1G of the reagent for $42.305. Empirical formula: C13H13IO8 Molecular weight: 424.14 MP: 130-133ºC Spectroscopic data: 1HNMR(CDCl3, ∂): 8.31 (d, J=8.5 Hz), 8.07 (t., J=8.5 and 7.3 Hz), 7.80 (t, J=8.5 and 7.3 Hz), 2.33 (s) and 2.01 (s) 13CNMR (CDCl3. ∂): 175.7, 174.0, 166.1, 142.4, 135.8, 133.8, 131.8, 126.5, 126.0, 20.4, 20 References.htmlhttp://www.umich.edu/~chemh215/W11HTML/SSG4/ssg4.5/References.html#widget1shapeimage_2_link_0shapeimage_2_link_1

Periodinane

Mechanism of Dess-Martin Oxidation

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