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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]
The third method involves treatment of acid chlorides: RC(O)Cl + H 2 O 2 → RCO 3 H + HCl. meta-Chloroperoxybenzoic acid (mCPBA) is prepared in this way: [7] m-chlorobenzoyl chloride + hydrogen peroxide → m-chloroperoxybenzoic acid. A related method starts with the peroxyanhydride. [8] Aromatic aldehydes can be autoxidized to give ...
A widely used peroxy acid for this reaction is meta-chloroperoxybenzoic acid (m-CPBA), due to its stability and good solubility in most organic solvents. [1] [3] The reaction is performed in inert solvents (C 6 H 14, C 6 H 6, CH 2 Cl 2, CHCl 3, CCl 4) between -10 and 60 °C with the yield of 60-80%.
Other raw materials required for this synthesis include 4-pentenal, m-chloroperoxybenzoic acid, methyl magnesium bromide and phosgene. Two key chemical transformations in this sequence are a Chan rearrangement and a sulfonyloxaziridine enolate oxidation.
The epoxidation of allylic alcohols is a class of epoxidation reactions in organic chemistry.One implementation of this reaction is the Sharpless epoxidation.Early work showed that allylic alcohols give facial selectivity when using meta-chloroperoxybenzoic acid (m-CPBA) as an oxidant.
The original implementations of the Rubottom oxidation featured the peroxyacid meta-chloroperoxybenzoic acid (mCPBA) as the oxidant in dichloromethane (DCM), in the case of Hassner and Brook, and hexanes for Rubottom.
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 Wharton reaction also commonly suffers from reduction of the allylic alcohol product down to the aliphatic alcohol.
This page was last edited on 6 December 2021, at 01:46 (UTC).; Text is available under the Creative Commons Attribution-ShareAlike 4.0 License; additional terms may apply.
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