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An illustrative example is the epoxidation of trans-2-butene with m-CPBA to give trans-2,3-epoxybutane: [4] The oxygen atom that adds across the double bond of the alkene is taken from the peroxy acid, generating a molecule of the corresponding carboxylic acid as a byproduct.
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 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.
The products of the Baeyer–Villiger oxidation are believed to be controlled through both primary and secondary stereoelectronic effects. [4] The primary stereoelectronic effect in the Baeyer–Villiger oxidation refers to the necessity of the oxygen-oxygen bond in the peroxide group to be antiperiplanar to the group that migrates.
Alkenes bound to both electron-withdrawing and -donating groups tend to behave like the former, requiring long oxidation times and occasionally some heating. Like electron-poor epoxides, epoxide products from this class of substrates are often stable with respect to hydrolysis.
Many common phenomena can be attributed to autoxidation, such as food going rancid, [2] the 'drying' of varnishes and paints, and the perishing of rubber. [3] It is also an important concept in both industrial chemistry and biology. [4] Autoxidation is therefore a fairly broad term and can encompass examples of photooxygenation and catalytic ...
Below are some representative Rubottom oxidation products synthesized in the seminal papers. [ 6 ] [ 11 ] [ 12 ] In 1978, Rubottom showed that siloxy 1,3 dienes, derived from acyclic or cyclic enones could also serve as substrates for the Rubottom oxidation to forge α-hydroxy enones after treatment with triethyl ammonium fluoride.
A generic epoxide. In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen.This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers.