Dess-Martin Periodinane

Title: Dess-Martin Periodinane
CAS Registry Number: 87413-09-0
CAS Name: 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one
Additional Names: triacetoxyperiodinane
Molecular Formula: C13H13IO8
Molecular Weight: 424.14
Percent Composition: C 36.81%, H 3.09%, I 29.92%, O 30.18%
Literature References: Pentacoordinate organoiodine (periodinane); selectively oxidizes primary and secondary alcohols, aldehydes and ketones. Prepn: D. B. Dess, J. C. Martin, J. Org. Chem. 48, 4155 (1983); R. E. Ireland, L. Liu, ibid. 58, 2899 (1993). Structure and reaction conditions: D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 113, 7277 (1991); acceleration by water: S. D. Meyer, S. L. Schreiber, J. Org. Chem. 59, 7549 (1994). Synthetic applications: N. E. Jenkins et al., Synth. Commun. 30, 947 (2000); A. G. Myers et al., Tetrahedron Lett. 41, 1359 (2000).
Properties: White crystalline solid, mp 134°. Sparingly sol in hexane or ether. Sol in chloroform, methylene chloride, acetonitrile and acetone.
Melting point: mp 134°
Use: Oxidizing reagent.
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