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Sodium periodate is an inorganic salt, composed of a sodium cation and the periodate anion.It may also be regarded as the sodium salt of periodic acid.Like many periodates, it can exist in two different forms: sodium metaperiodate (formula NaIO 4) and sodium orthoperiodate (normally Na 2 H 3 IO 6, but sometimes the fully reacted salt Na 5 IO 6).
Classically, periodate was most commonly produced in the form of sodium hydrogen periodate (Na 3 H 2 IO 6). [2] This is commercially available, but can also be produced by the oxidation of iodates with chlorine and sodium hydroxide. [3] Or, similarly, from iodides by oxidation with bromine and sodium hydroxide:
The development of the Lemieux–Johnson oxidation was preceded by an analogous process, developed by Lemieux and Ernst Von Rudloff (sometimes called the Lemieux-Von Rudloff reaction), which used an aqueous solution of sodium periodate with a low (catalytic) concentration of potassium permanganate. [7]
Through a variety of mechanisms, the removal of a hydride equivalent converts a primary or secondary alcohol to an aldehyde or ketone, respectively. The oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (gem-diol, R-CH(OH) 2) by reaction with water ...
The mechanism consists of four steps: Oxidative ionization of two sodium atoms on the double bond of two ester molecules. Wurtz-type coupling between two molecules of the homolytic ester derivative. Alkoxy-eliminations in both sides occur, producing a 1,2-diketone. Oxidative ionization of two sodium atoms on both diketone double bonds. The ...
In combination with sodium periodate, OsO 4 is used for the oxidative cleavage of alkenes (Lemieux-Johnson oxidation) when the periodate serves both to cleave the diol formed by dihydroxylation, and to reoxidize the OsO 3 back to OsO 4. The net transformation is identical to that produced by ozonolysis. Below an example from the total synthesis ...
Sodium periodate oxidizes the sialic acids on glycoproteins to aldehydes to form these stable linkages at pH 4–6. Polyclonal antibodies are heavily glycosylated, and because glycosylation does not interfere with the antibody activity, biotinylating the glycosyl groups is an ideal strategy to generate biotinylated antibodies.
The first periodatonickalates discovered were sodium nickel periodate (NaNiIO 6 ·0.5H 2 O) and potassium nickel periodate (KNiIO 6 ·0.5H 2 O). P. Ray and B. Sarma obtained these dark purple double salts in 1949, mixing nickel sulfate with potassium or sodium periodate and (as oxidant) a boiling aqueous solution of an alkali persulfate ...