Iodoxy benzoic acid

Product 24 contains a secondary alcohol at the position where the primary alcohol was in substrate 23. From that it can be seen that 23 is first converted into the corresponding aldehyde, which then acts as electrophile in the following aldol reaction. Here, oxidation to the aldehyde is performed with the iodo(V)-reagent IBX (o-iodoxy-benzoic acid, 51). After addition-elimination, species 52 is formed, which disproportionates to the iodo(III)-compound 53 and the desired aldehyde 38. 

A new, eco-friendly o-iodoxy benzoic acid-mediated synthesis of 3,5-dia-rylisoxazoles and 5-arylisoxazole-3-carboxylic acids from a,p-unsaturated ketoximes has been reported (14SC1453). 

Hantzsch 1,4-dihydropyridines with o-iodoxy-benzoic acid in water/acetone. 

Some A -iodane derivatives are very useful oxidizing reagents in organic synthesis, e.g., 2-iodoxy-benzoic acid (IBX) and the Dess-Martin reagent (DMP) effectively convert primary and secondary alcohols to aldehydes and ketones, respectively [104]. Also directional preferences of short contacts observed in the sohd between electron rich sites and iodine of some A -iodane derivatives are nicely consistent with an asymmetric electron density distribution on iodine resulting in the presence of most positive regions on the covalent bonds extensions, and the preferential entrance of nucleophiles in these regions [105]. For instance, the o-hole model predicts that in the spirocyclic compound shown in Fig. 17, the electrostatic... 

Kennedy and Stock reported the first use of Oxone for many common oxidation reactions such as formation of benzoic acid from toluene and of benzaldehyde, of ben-zophenone from diphenyhnethane, of frawi-cyclohexanediol Ifom cyclohexene, of acetone from 2-propanol, of hydroquinone from phenol, of e-caprolactone from cyclohexanone, of pyrocatechol from salicylaldehyde, of p-dinitrosobenzene from p-phenylenediamine, of phenylacetic acid from 2-phenethylamine, of dodecylsulfonic acid from dodecyl mercaptan, of diphenyl sulfone from diphenyl sulfide, of triphenylphosphine oxide from triphenylphosphine, of iodoxy benzene from iodobenzene, of benzyl chloride from toluene using NaCl and Oxone and bromination of 2-octene using KBr and Oxone . Thus, they... 

---