m-Chloroperoxybenzoic Acid (MCPBA)

Introduction

MCPBA is a strong electrophilic oxidising agent. It is a white powder (mp 90 °C), easy to handle, flammable, ­hygroscopic, soluble in less-polar solvents like CH₂Cl₂, CHCl₃, 1,2-DCE, EtOAc, EtOH, t-BuOH, Et₂O and some nonpolar solvents like benzene, it is slightly soluble in hexane, CCl₄ and insoluble in H₂O. Pure MCPBA is shock-sensitive and can deflagrate, it is potentially explosive beyond 85% purity. It shows 1% degradation per year at room temperature. It is widely used in organic chemistry to carry out a variety of chemical transformations such as oxidation of carbonyl compounds, iminoindolines, olefins, imines, alkanes, silyl enol ethers, N- and S-hetero­cycles, active methylene groups, fluoromethylated allylic bromides, cyclic acetals and N-substituted phthal­imidines, etc. [1a] Besides these it also oxidises selenides, furans and phosphates to selenoxides, pyranones and phosphates, respectively. It is superior to H₂O₂ and other oxidising agents because of its reactivity, stereoselec­tivity, purity and yield of products. [1b]

References

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