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The reaction proceeds through what is commonly known as the "butterfly mechanism", first proposed by Bartlett, wherein the peracid is intramolecularly hydrogen-bonded at the transition state. [5] Although there are frontier orbital interactions in both directions, the peracid is generally viewed as the electrophile and the alkene as the ...
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]
Original reactions reported by Baeyer and Villiger. There were three suggested reaction mechanisms of the Baeyer–Villiger oxidation that seemed to fit with observed reaction outcomes. [16] These three reaction mechanisms can really be split into two pathways of peroxyacid attack – on either the oxygen or the carbon of the carbonyl group. [17]
A second significant side reaction in reactions of ketones and aldehydes is selanylation of the intermediate selenoxide. This process leads to elimination products retaining a carbon-selenium bond, [16] and is more difficult to prevent than the seleno-Pummerer reaction. Tertiary selenoxides, which are unable to undergo enolization, do not react ...
Although the presence of an allylic alcohol does lead to increased stereoselectivity, the rates of these reactions are slower than systems lacking alcohols. However, the reaction rates of substrates with a hydrogen bonding group are still faster than the equivalent protected substrates. This observation is attributed to a balance of two factors.
The metal-mediated processes include a carbonyl-olefination and an olefin–olefin metathesis event. There are two general mechanistic schemes to perform this overall transformation: one, reaction of a [M=CHR 1] reagent with an alkene to generate a new metal alkylidene, which then couples with a carbonyl group to form the desired substituted alkene and an inactive [M=O] species (type A); two ...
A generalized mechanism of the Buchner ring expansion. A common method for expanding a ring involves opening cyclopropane-containing bicyclic intermediate. The strategy can start with a Simmons-Smith-like cyclopropanation of a cyclic alkene. [8] A related cyclopropane-based ring expansion is the Buchner ring expansion.
While the Rubottom oxidation generally gives good yields and is highly scalable (see 2S-hydroxymutilin synthesis), there are still some problems with the reaction. As mentioned above, the acidic reaction conditions are not tolerated by many complex substrates, but this can be abrogated with the use of buffer systems. [ 1 ]
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