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![Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
Dess-Martin periodinane is useful for the facile and efficient oxidation of primary alcohols to aldehydes and secondary alcohols to ketones. Dess-Martin periodinane reacts much more rapidly with benzylic alcohols than with saturated alkanols, but shows no selectivity between 2-propanol and ethanol—the basis for selectivity is not yet understood. The reaction is catalyzed by acid or excess alcohol. In a typical experiment, a solution of 3,4,5-trimethoxybenzyl alcohol in methylene chloride was added to a solution of Dess-Martin periodinane (2). After 20 minutes the homogenous mixture was diluted with ether and the resulting suspension of the iodinane (3) was added to sodium hydroxide to hydrolyze the iodinane to yield 2-iodosobenzoate.
Fan, X. S.; He, Y.; Qu Y. Y.; Wang, J. J.; Wang, Y. Y.; Xu, H. Y.; Zhang, X. Y. J. Org. Chem. 2011, 76, 982-985.
The fact that CrO3 alone is not as effective as the Dess-Martin periodinane in the formation of a pyrano[2,3-d]pyrimidine-2,5-dione nucleoside suggests that the acetic acid formed in the oxidation process with Dess-Martin periodinane plays an important role, which is most likely attributed to its capability as an acid in facilitating the keto-enol tautomerism. The acid may also play a catalytic role in generating and activating the allene and facilitating olefin isomerization.
Inoue, R.; Ishikawa, S.; Kamimura, A.; Nakayama, M.; Nozaki, Y. Tetrahedron Lett. 2011, 52, 538-540.
A wide range of oxidants have been used in the lab, such as swern and PCC. Tetrapropylammonium perruthenate (TPAP/NMO) and Dess–Martin periodinane (DMP) are improved oxidants for mild oxidation of alcohols.
Zhdankin, V. V. J. Org. Chem. 2011, 76, 1185-1197.
This paper cites states that Dess and J. C. Martin initiated interest in organoiodine(V) reagents when they described a two-step synthesis of an organoiodine(V) compound, which is widely used in organic syntheses and is one of the most cited papers ever published in J. Org. Chem.](References_files/shapeimage_3.png)
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< http://www.org-chem.org/yuuki/acid/acid_en.html>.
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