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The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant. [1] The reaction is named after Adolf von Baeyer and Victor Villiger who first reported the reaction in 1899. [1] Baeyer-Villiger oxidation
The most common use of organic peroxy acids is for the conversion of alkenes to epoxides, the Prilezhaev reaction. Formation of an epoxide from an alkene and a peroxycarboxylic acid. Another common reaction is conversion of cyclic ketones to the ring-expanded esters using peracids in a Baeyer-Villiger oxidation .
The Prilezhaev reaction, also known as the Prileschajew reaction or Prilezhaev epoxidation, is the chemical reaction of an alkene with a peroxy acid to form epoxides. [1] It is named after Nikolai Prilezhaev , who first reported this reaction in 1909. [ 2 ]
Alkenes react with percarboxylic acids and even hydrogen peroxide to yield epoxides: RCH=CH 2 + RCO 3 H → RCHOCH 2 + RCO 2 H. For ethylene, the epoxidation is conducted on a very large scale industrially using oxygen in the presence of silver-based catalysts: C 2 H 4 + 1/ 2 O 2 → C 2 H 4 O. Alkenes react with ozone, leading to the scission ...
The main areas of use are the conversion of ketones to esters (Baeyer-Villiger oxidation), epoxidation of alkenes (Prilezhaev reaction), conversion of silyl enol ethers to silyl α-hydroxy ketones (Rubottom oxidation), oxidation of sulfides to sulfoxides and sulfones, and oxidation of amines to produce amine oxides.
An enal (or alkenal) is an organic compound containing both alkene and aldehyde functional groups. In an α,β-unsaturated enal, the alkene is conjugated to the carbonyl group of the aldehyde (formyl group). [3] The simplest enal is acrolein (CH 2 =CHCHO). Other examples include cis-3-hexenal (essence of mowed lawns) and cinnamaldehyde (essence ...
The radicals formed from alkenyl peroxides can be utilized in organic radical reactions. For example, they can mediate hydrogen atom abstraction reactions and thus lead to the functionalization of C-H bonds, [7] or they can be used to introduce ketone residues by addition of the alkenyloxyl radicals to alkenes. [8] [9] [10]
Heating may be used to encourage oxidation, although the reaction temperature should never exceed 50 °C, to avoid decomposition of the dioxirane [1] Alkenes bound to both electron-withdrawing and -donating groups tend to behave like the former, requiring long oxidation times and occasionally some heating.