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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.
Babler-Dauben oxidation of cyclic tertiary allylic alcohols. The reaction produces the desired enone product to high yield (typically >75%), is operationally simple and does not require air-free techniques or heating. [1] It suffers, however, from the very high toxicity and environmental hazard posed by the hexavalent chromium PCC oxidising ...
The Parikh–Doering oxidation is an oxidation reaction that transforms primary and secondary alcohols into aldehydes and ketones, respectively. [1] The procedure uses dimethyl sulfoxide (DMSO) as the oxidant and the solvent, activated by the sulfur trioxide pyridine complex (SO 3 •C 5 H 5 N) in the presence of triethylamine or diisopropylethylamine as base.
The direct oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (R−CH(OH) 2) by reaction with water before it can be further oxidized to the carboxylic acid. Mechanism of oxidation of primary alcohols to carboxylic acids via aldehydes and aldehyde hydrates
The Jones oxidation is an organic reaction for the oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively. It is named after its discoverer, Sir Ewart Jones . The reaction was an early method for the oxidation of alcohols.
In organic chemistry, the Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol (−OH) is oxidized to an aldehyde (−CH=O) or ketone (>C=O) using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine.
An Oppenauer oxidation of aldehyde. Another side reaction is the Tischenko reaction of aldehyde products with no α-hydrogen, but this can be prevented by use of anhydrous solvents. [4] Another general side reaction is the migration of the double bond during the oxidation of allylic alcohol substrates. [14] Oppenauer oxidation of a steroid ...
The sulfonium oxidations can be categorized into two groups: The methods discovered earliest rely on activated alcohols like alkyl tosylates (Kornblum oxidation) [2] or alkyl chloroformates (from reaction of alcohols with phosgene: Barton-Kornblum) [3] that react as electrophiles when treated with DMSO, liberating an oxygenated leaving group (e.g. OTs−).