What is mCPBA used for in organic chemistry?

mCPBA is widely used for chemical transformations such as the oxidation of carbonyl compounds, iminoindolines, olefins, imines, alkanes, silyl enol ethers, N- and S-heterocycles, active methylene groups, fluoromethylated allylic bromides, cyclic acetals, N-substituted phthalimidines, selenides, furans and phosphates.

Is mCPBA an oxidation?

mCPBA is often preferred to other peroxy acids because of its relative ease of handling. mCPBA is a strong oxidizing agent that may cause fire upon contact with flammable material.

What does mCPBA do to an aldehyde?

Abstract. Purified mCPBA is a useful reagent for the oxidation of several classes of aldehydes. α-Branched aliphatic aldehydes undergo Baeyer–Villiger oxidation to give formates. α-Branched α,β-unsaturated aldehydes provide enolformates and/or epoxides, and α-hydroxylated aldehydes give rise to ketones.

How is epoxidation of alkenes done with mCPBA?

This is usually done with peroxyacids such as MCPBA ( meta -chloroperoxy benzoic acid) or Peroxyacetic acid: The mechanism of epoxidation is similar to the formation of halonium ion and oxymercuration that we discussed in the other addition reactions of alkenes.

How are alkenes oxidized to epoxides in organic chemistry?

Epoxidation of alkenes Alkenes can be oxidized to epoxides using a ‘ peroxyacid ‘ such as m -chloroperoxybenzoic acid (MCPBA). Notice the presence of a third oxygen in the peroxyacid functional group. The mechanism was covered earlier in section 10.7.

What kind of reaction does mCPBA have with hydroxide?

Mostly, they are good electrophiles that will react with nucleophiles such as Grignard or organolithium reagents, hydroxide or alkoxide ions, or (in the presence of acid) water. Another useful reaction of mCPBA – commonly encountered in Org 2 – is the Baeyer-Villiger reaction.

How is m CPBA a functional group tolerant oxidant?

An oxidative ring contraction of easily accessible cyclobutene derivatives enables a selective formation of cyclopropylketones in the presence of m CPBA as oxidant. This functional group tolerant transformation proceeds under mild conditions at room temperature.