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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 ]
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 .
Trifluoroperacetic acid (trifluoroperoxyacetic acid, TFPAA) is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula CF 3 COOOH . [ Note 1 ] It is a strong oxidizing agent for organic oxidation reactions, such as in Baeyer–Villiger oxidations of ketones . [ 1 ]
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.
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 ...
Magnesium monoperoxyphthalate (MMPP) is a water-soluble peroxy acid used as an oxidant in organic synthesis.Its main areas of use are the conversion of ketones to esters (Baeyer-Villiger oxidation), epoxidation of alkenes (Prilezhaev reaction), oxidation of sulfides to sulfoxides and sulfones, oxidation of amines to produce amine oxides, and in the oxidative cleavage of hydrazones.
Illustrative is the epoxidation of styrene with perbenzoic acid to styrene oxide: [12] The stereochemistry of the reaction is quite sensitive. Depending on the mechanism of the reaction and the geometry of the alkene starting material, cis and/or trans epoxide diastereomers may be formed. In addition, if there are other stereocenters present in ...
Peracetic acid (also known as peroxyacetic acid, or PAA) is an organic compound with the formula CH 3 CO 3 H. This peroxy acid is a colorless liquid with a characteristic acrid odor reminiscent of acetic acid. It can be highly corrosive. Peracetic acid is a weaker acid than the parent acetic acid, with a pK a of 8.2. [2]