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Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
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. Periodic acid was discovered by Heinrich Gustav Magnus and C. F ...
LiBr reacts with NaIO 4 and acetic acid to produce lithium acetate, which can then proceed through the reaction as previously mentioned. The protocol produced high dr for the corresponding diol, depending on the oxidant chosen. The modification of the Prevost-Woodward reaction proposed by Sudalai.
Dess–Martin periodinane (DMP) is a chemical reagent used in the Dess–Martin oxidation, oxidizing primary alcohols to aldehydes and secondary alcohols to ketones. [1] [2] This periodinane has several advantages over chromium- and DMSO-based oxidants that include milder conditions (room temperature, neutral pH), shorter reaction times, higher yields, simplified workups, high chemoselectivity ...
The chemical reaction called Sharpless asymmetric dihydroxylation can be used to produce chiral diols from alkenes using an osmate reagent and a chiral catalyst. 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.
The carbon–carbon bond in a vicinal diol (glycol) is cleaved and instead the two oxygen atoms become double-bonded to their respective carbon atoms. Depending on the substitution pattern in the diol, these carbonyls will be ketones and/or aldehydes. [1] Glycol cleavage is an important for determining the structures of sugars.
An α,β-epoxyketone reacts with hydrazine hydrate to yield an allylic alcohol. [7] In the synthesis of warburganal, a bioactive natural product, the α,β-epoxyketone is formed from a cyclic α,β-unsaturated ketone and in a separate step reacts under the classical Wharton olefin synthesis conditions to yield an allylic diol. [8]