• Hydroxamic acids are oxidized to acyl nitroso compounds which can undergo cycloaddition to dienes: Synth. Commun., 30, 47 (2000).
• Deprotection of thioacetals can be accomplished under extremely mild conditions: Org. Lett., 5, 575 (2003).
• For a detailed discussion of the scope and advantages of this reagent, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 7, p. 4982.
• For use in the synthesis of imides, N-acyl vinylogous carbamates and ureas, and nitriles, by oxidation of amides and amines, see: Angew. Chem. Int. Ed., 44, 5992 (2005).
• ɑ,?-Unsaturated carboxylic acids undergo Hunsdiecker-type decaboxylative bromination with tetraethylammonium bromide in the presence of the reagent: Synlett, 2495 (2005).
• One of the mildest reagents for the selective oxidation of primary and secondary alcohols to aldehydes and ketones. High yields can be obtained at ambient temperatures, under neutral conditions, in chloroform, dichloromethane or acetonitrile: J. Org. Chem., 48, 4155 (1983); J. Am. Chem. Soc., 113, 7277 (1991); (reviews): J. Prakt. Chem./Chem. Ztg., 338, 588 (1996); Synlett, 278 (2000). Has been employed for the oxidation of a wide variety of sensitive substrates and is particularly valuable in multi-step syntheses of polyfunctional molecules with complex stereochemistry. For an example involving exclusive oxidation of one of four possible secondary OH groups in a synthesis of erythromycin B, see: J. Am. Chem. Soc., 119, 3193 (1997). Allylic and benzylic alcohols can be oxidized selectively in the presence of saturated alcohols, and give the carbonyl compounds cleanly without over-oxidation or cis-trans isomerization: Tetrahedron Lett., 29, 995 (1988); J. Org. Chem., 55, 1636 (1990).
• CAUTION! In the presence of moisture, may form iodoxybenzoic acid which has been reported to be explosive under excessive heating or impact: Chem. Eng. News, 68(29), 3 (1990).
• Has also been used for deoximation of ketoximes to ketones under mild conditions: Tetrahedron Lett., 39, 3209 (1998); Synthesis, 760 (1999).
Oxidising (O)
Harmful (Xn)
Irritant (Xi)