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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).
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. Thus, the oxidation of a primary alcohol at the aldehyde level without further oxidation to the carboxylic acid is possible by performing the reaction ...
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 classical Lemieux–Johnson oxidation often generates many side products, resulting in low reaction yields; however the addition of non-nucleophilic bases, such as 2,6-lutidine, can improve on this. [3] OsO 4 may be replaced with a number of other Osmium compounds. [4] [5] Periodate may also be replaced with other oxidising agents, such as ...
Illustrative is the oxidation of the following diol to a carboxylic acid: Oxidation of epoxy alcohols also ... by the addition of sodium periodate to ...
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 ...
In organic chemistry, the Malaprade reaction or Malaprade oxidation is a glycol cleavage reaction in which a vicinal diol is oxidized by periodic acid or a periodate salt to give the corresponding carbonyl functional groups. [1] [2] The reaction was first reported by Léon Malaprade in 1928. [3] [4] Amino alcohols are also cleaved. [5]
Diols can also be used to protect carbonyl groups. [14] They are commonly used and are quite efficient at synthesizing cyclic acetals. These protect the carbonyl groups from reacting from any further synthesis until it is necessary to remove them. The reaction below depicts a diol being used to protect a carbonyl using zirconium tetrachloride. [15]