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meta-Chloroperoxybenzoic acid (mCPBA or mCPBA) is a peroxycarboxylic acid. It is a white solid often used widely as an oxidant in organic synthesis. mCPBA is often preferred to other peroxy acids because of its relative ease of handling. [1] mCPBA is a strong oxidizing agent that may cause fire upon contact with flammable material. [2]
Through a concerted mechanism, one of the substituents on the ketone group migrates to the oxygen of the peroxide group while a carboxylic acid leaves. [1] This migration step is thought to be the rate determining step. [2] [3] Finally, deprotonation of the oxocarbenium ion produces the ester. [1] Reaction mechanism of the Baeyer-Villiger ...
The reaction proceeds through what is commonly known as the "butterfly mechanism", first proposed by Bartlett, wherein the peracid is intramolecularly hydrogen-bonded at the transition state. [5] Although there are frontier orbital interactions in both directions, the peracid is generally viewed as the electrophile and the alkene as the ...
The Chugaev elimination is a chemical reaction that involves the elimination of water from alcohols to produce alkenes.The intermediate is a xanthate.It is named for its discoverer, the Russian chemist Lev Aleksandrovich Chugaev (1873–1922), who first reported the reaction sequence in 1899.
The mechanism of epoxidation with dioxiranes likely involves concerted oxygen transfer through a spiro transition state. As oxygen transfer occurs, the plane of the oxirane is perpendicular to and bisects the plane of the alkene pi system. The configuration of the alkene is maintained in the product, ruling out long-lived radical intermediates.
In the elimination reaction, all five participating reaction centers are coplanar and, therefore, the reaction stereochemistry is syn. Oxidizing agents used are hydrogen peroxide, ozone or MCPBA. This reaction type is often used with ketones leading to enones. An example is acetylcyclohexanone elimination with benzeneselenylchloride and sodium ...
The mechanism of the Wharton reaction. The Wharton olefin synthesis allows the transformation of an α,β unsaturated ketone into an allylic alcohol. The epoxide starting material can be generated by a number of methods, with the most common being reaction of the corresponding alkene with hydrogen peroxide or m-chloroperoxybenzoic acid. The ...
The Juliá–Colonna epoxidation is an asymmetric poly-leucine catalyzed nucleophilic epoxidation of electron deficient olefins in a triphasic system.The reaction was reported by Sebastian Juliá at the Chemical Institute of Sarriá in 1980, [1] with further elaboration by both Juliá and Stefano Colonna (Istituto di Chimica Industriale dell'Università, Milan, Italy).