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In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon.
Thiol-ene reactions are known to proceed through a Michael addition pathway. These reactions are catalyzed by either a base or a nucleophile, resulting in a similar anti-Markovnikov addition product as the thiol-ene radical addition.
Nucleophilic conjugate addition is a type of organic reaction. Ordinary nucleophilic additions or 1,2-nucleophilic additions deal mostly with additions to carbonyl compounds. Simple alkene compounds do not show 1,2 reactivity due to lack of polarity , unless the alkene is activated with special substituents .
NEM is a Michael acceptor in the Michael reaction, which means that it adds nucleophiles such as thiols. The resulting thioether features a strong C–S bond and the reaction is virtually irreversible. Reaction with thiols occur in the pH range 6.5–7.5, NEM may
Arthur Michael is remembered today primarily for the Michael reaction, also called the Michael addition. As originally defined by Michael, the reaction involves the combination of an enolate ion of a ketone or aldehyde to an α,β-unsaturated carbonyl compound at the β carbon. [6] Michael was also well known in his day for incorporating ...
One type of conjugate addition is the Michael addition, which is used commercially in the conversion of mesityl oxide into isophorone. Owing to their extended conjugation, α,β-unsaturated carbonyls are prone to polymerization. In terms of industrial scale, polymerization dominates the use of α,β-unsaturated carbonyls.
Such reactions are conducted in the presence of acidic catalysts. The other principal route to thiols involves the addition of hydrogen sulfide to alkenes. Such reactions are usually conducted in the presence of an acid catalyst or UV light. Halide displacement, using the suitable organic halide and sodium hydrogen sulfide has also been used. [23]
Michael addition; Michael addition, Michael system; Michael condensation; Michaelis–Arbuzov reaction; Midland Alpine borane reduction; Mignonac reaction; Milas hydroxylation of olefins; Minisci reaction; Mislow–Evans rearrangement; Mitsunobu reaction; Miyaura borylation; Modified Wittig-Claisen tandem reaction; Molisch's test; Mozingo reduction