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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]
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 ...
The Criegee oxidation is a glycol cleavage reaction in which vicinal diols are oxidized to form ketones and aldehydes using lead tetraacetate.It is analogous to the use of periodate (Malaprade reaction) but uses a milder oxidant.
Periodic acid (/ ˌ p ɜːr aɪ ˈ ɒ d ɪ k / per-eye-OD-ik) is the highest oxoacid of iodine, in which the iodine exists in oxidation state +7. It can exist in two forms: orthoperiodic acid, with the chemical formula H 5 IO 6 , and metaperiodic acid, which has the formula HIO 4 .
Dihydroxylation is the process by which an alkene is converted into a vicinal diol.Although there are many routes to accomplish this oxidation, the most common and direct processes use a high-oxidation-state transition metal (typically osmium or manganese).
In cyclic systems, the reaction presents more features of interest. In these reactions, the stereochemistry of the diol plays a crucial role in deciding the major product. An alkyl group which is situated trans- to the leaving –OH group may migrate to the carbocation center, but cis- alkyl groups migrate at a very low rate.
Another method is the Woodward cis-hydroxylation (cis diol) and the related Prévost reaction (anti diol), which both use iodine and the silver salt of a carboxylic acid. A route to synthesizing cis-1,2-diols using osmium tetraoxide An example of Prévost reaction used to synthesize anti diol
The most reactive metals, such as sodium, will react with cold water to produce hydrogen and the metal hydroxide: . 2 Na (s) + 2 H 2 O (l) →2 NaOH (aq) + H 2 (g). Metals in the middle of the reactivity series, such as iron, will react with acids such as sulfuric acid (but not water at normal temperatures) to give hydrogen and a metal salt, such as iron(II) sulfate:
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