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The Prilezhaev reaction, also known as the Prileschajew reaction or Prilezhaev epoxidation, is the chemical reaction of an alkene with a peroxy acid to form epoxides. [1] It is named after Nikolai Prilezhaev, who first reported this reaction in 1909. [2]
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 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.
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 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 ...
Selenoxide elimination (also called α-selenation) [1] is a method for the chemical synthesis of alkenes from selenoxides. It is most commonly used to synthesize α,β-unsaturated carbonyl compounds from the corresponding saturated analogues. [2] It is mechanistically related to the Cope reaction.
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Diastereoselective epoxidation may be achieved through the use of alkene starting materials with diastereotopic faces. When racemic 3-isopropylcyclohexene was subjected to DMD oxidation, the trans epoxide, which resulted from attack on the less hindered face of the double bond, was the major product.