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Methyl vinyl ketone

About: Methyl vinyl ketone is a research topic. Over the lifetime, 1510 publications have been published within this topic receiving 26839 citations. The topic is also known as: 3-buten-2-one & gamma-oxo-alpha-butylene.


Papers
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Journal ArticleDOI
TL;DR: The polystyrene-supported N-alkylimidazole-based dendritic catalysts for the Baylis-Hillman reaction exhibit one of the strongest beneficial effects of multivalent architecture ever reported for an organocatalyst.
Abstract: The polystyrene-supported N-alkylimidazole-based dendritic catalysts for the Baylis-Hillman reaction exhibit one of the strongest beneficial effects of multivalent architecture ever reported for an organocatalyst. The yields in the model reaction of methyl vinyl ketone with p-nitrobenzaldehyde are more than tripled when a non-dendritic catalyst is replaced by a second- or third-generation analogue. Moreover, the reaction of the less active substrates will not occur with the non-dendritic catalyst and will proceed to a significant extent only with the analogous catalysts of higher generations. A substantial additional enhancement of the reaction yield could be achieved by increasing the content of water in the reaction solvent. The plausible cause of the dendritic effect is the assistance of the second, nearby imidazole moiety in the presumably rate-determining proton transfer in the intermediate adduct, after the first imidazole unit induced the formation of the new carbon-carbon bond.

10 citations

Journal ArticleDOI
TL;DR: The use of structurally well-defined chiral chiral [CuCl 2 (sparteine) 1 and [NiCl 2(sparteines) 2 complexes as catalysts under fluoride anion-promoted double catalytic activation (DCA) conditions caused enantioreversal in the asymmetric Mukaiyama aldol reaction of 1-phenyl-1-trimethylsiloxyethylene with various aromatic aldehydes as mentioned in this paper.
Abstract: The use of structurally well-defined chiral [CuCl 2 (sparteine)] 1 and [NiCl 2 (sparteine)] 2 complexes as catalysts under fluoride anion-promoted double catalytic activation (DCA) conditions cause enantioreversal in the asymmetric Mukaiyama aldol reaction of 1-phenyl-1-trimethylsiloxyethylene with various aromatic aldehydes. A similar enantioreversal also occurs in the direct aldol reaction between methyl vinyl ketone and various aromatic aldehydes under Et 3 N promoted DCA conditions. We have quantitatively analyzed using group theoretical analysis via symmetry deformation coordinates, the molecular structures of 1 and 2 from the X-ray structural data; the results from the study show that the innate stereochemical differences that are present in their molecular structures, form the basis for the enantioreversal phenomenon in the asymmetric C–C bond-forming aldol reactions.

9 citations

Journal ArticleDOI
TL;DR: The pentacovalent oxaphospholene derived from methyl vinyl ketone and trialkyl phosphite has been shown to condense with a variety of electrophiles to produce highly substituted phosphonates as discussed by the authors.
Abstract: The pentacovalent oxaphospholene derived from methyl vinyl ketone and trialkyl phosphite has been shown to condense with a variety of electrophiles to produce highly substituted phosphonates.

9 citations

Patent
04 May 1973
TL;DR: In this paper, Copolymers including diallyldialkylammonium compounds of the formula: where R1 and R2 are independently selected from the group consisting of lower alkyl, halogen substituted lower alkl and phenyl and X is OH, a halogen or an inorganic or organic anion, alkenyl monomers such as methyl vinyl ketone and halogen containing vinyl monomers, are useful in the preparation of permoselective membranes.
Abstract: Copolymers including diallyldialkylammonium compounds of the formula: WHEREIN R1 and R2 are independently selected from the group consisting of lower alkyl, halogen substituted lower alkyl and phenyl and X is OH, a halogen or an inorganic or organic anion, alkenyl monomers, such as methyl vinyl ketone and halogen containing vinyl monomers, are useful in the preparation of anion permoselective membranes.

9 citations

Reference EntryDOI
TL;DR: Wieland Miescher ketone (WMK) as discussed by the authors, 1,3-cyclohexane-1.3-dione, methyl vinyl ketone.
Abstract: (S)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphtalenedione 2-Methyl-2-(3-oxobutyl)-1,3-cyclohexanedione 2-Methyl-1,3-cyclohexanedione N-Tosyl-(Sa)-binam-L-prolinamide Methyl vinyl ketone Keywords: Wieland Miescher ketone (WMK); fractional crystallization; natural product synthesis; 2- methylcyclohexane-1,3-dione; (S)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphtalenedione; N-tosyl-(Sa)-binam-L-prolinamide organocatalysis

9 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20238
202249
202121
202020
201910
201817