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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.
The second is the electron-withdrawing nature of the oxygen, which draws electron density away from the alkene, lowering its reactivity. [5] Acyclic allylic alcohols exhibit good selectivity as well. In these systems both A 1,2 (steric interactions with vinyl) and A 1,3 strain are considered.
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]
Although many different peroxyacids are used for the Baeyer–Villiger oxidation, some of the more common oxidants include meta-chloroperbenzoic acid (mCPBA) and trifluoroperacetic acid (TFPAA). [2] The general trend is that higher reactivity is correlated with lower pK a (i.e.: stronger acidity) of the corresponding carboxylic acid (or alcohol ...
The Sharpless epoxidation is viable with a large range of primary and secondary alkenic alcohols. Furthermore, with the exception noted above, a given dialkyl tartrate will preferentially add to the same face independent of the substitution on the alkene.To demonstrate the synthetic utility of the Sharpless epoxidation, the Sharpless group created synthetic intermediates of various natural ...
The silyl enol ether was then treated with excess mCPBA to facilitate a “double” Rubottom oxidation to give the exo product with both hydroxyl groups on the outside of the fused ring system. This dihydroxy product was then transformed into Velutinol A in three additional steps.
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.
The reverse or retro-Cope elimination has been reported, in which an N,N-disubstituted hydroxylamine reacts with an alkene to form a tertiary N-oxide. [ 9 ] [ 10 ] The reaction is a form of hydroamination and can be extended to the use of unsubstituted hydroxylamine, in which case oximes are produced.