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Methyl vinyl ketone (MVK, IUPAC name: butenone) is the organic compound with the formula CH 3 C(O)CH=CH 2. It is a reactive compound classified as an enone , in fact the simplest example thereof. It is a colorless, flammable, highly toxic liquid with a pungent odor.
Methacrolein, or methacrylaldehyde, is an unsaturated aldehyde.It is a clear, colorless, flammable liquid. Methacrolein is one of two major products resulting from the reaction of isoprene with OH in the atmosphere, the other product being methyl vinyl ketone (MVK, also known as butenone). [1]
The Wieland–Miescher ketone is the Robinson annulation product of 2-methyl-cyclohexane-1,3-dione and methyl vinyl ketone. This compound is used in the syntheses of many steroids possessing important biological properties and can be made enantiopure using proline catalysis.
The Robinson annulation, published by Robert Robinson in 1935, is a base-catalyzed reaction that combines a ketone and a methyl vinyl ketone (commonly abbreviated to MVK) to form a cyclohexenone fused ring system.
The reaction can be carried out in enantiomeric excess of up to 90% with the aid of bifunctional chiral BINOL and phosphinyl BINOL compounds, [2] for example in the reaction of n-(4-chloro-benzylidene)-benzenesulfonamide with methyl vinyl ketone (MVK) in cyclopentyl methyl ether and toluene at -15°C.
In organic chemistry, vinylation is the process of attaching a vinyl group (CH 2 =CH−) to a substrate. Many organic compounds contain vinyl groups, so the process has attracted significant interest, especially since the reaction scope includes substituted vinyl groups. The reactions can be classified according to the source of the vinyl group.
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For example, in the three-component coupling of aldehydes, amines, and activated alkenes, the aldehyde reacts with the amine to produce an imine prior to forming the aza-MBH adduct, as in the reaction of aryl aldehydes, diphenylphosphinamide, and methyl vinyl ketone, in the presence of TiCl 4, triphenylphosphine, and triethylamine: [19]