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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.


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Journal ArticleDOI
TL;DR: 2-Azabicyclo[2.2.1.2]oct-5-enes bearing an endo alkenyl substituent were synthesized by Diels-Alder addition of methyl vinyl ketone to a 1,6-dihydropyridine derived from methyl nicotinate, and the new 2-azatetracyclo structures formed in the photochemical reactions are thermally stable.
Abstract: 2-Azabicyclo[2.2.2]oct-5-enes bearing an endo alkenyl substituent were synthesized by Diels−Alder addition of methyl vinyl ketone to a 1,6-dihydropyridine derived from methyl nicotinate. Although 1,5-dienes with this skeleton were unreactive under thermal conditions, they were photochemically reactive. Irradiation of these dienes through a Corex filter resulted in intramolecular [2 + 2] cycloaddition to give “parallel” and “crossed” photoadducts along with small amounts of a hexahydroisoquinoline. The latter is thought to represent leakage of a diradical intermediate responsible for the parallel photoadduct. The new 2-azatetracyclo[4.4.0.0.4,907,10]decane and 3-azatetracyclo[6.1.1.0.2,705,9]decane structures formed in the photochemical reactions are thermally stable.

8 citations

Journal ArticleDOI
TL;DR: In this paper, a modified ZrO2 base was used for the double-bond isomerization of 1-butene and the liquid-phase Michael addition of 2-methylcyclohexane-1,3-dione to methyl vinyl ketone at room temperature.
Abstract: Potassium-modified ZrO2 base catalysts were prepared by wet impregnation of hydrous zirconia and anhydrous zirconia with potassium compounds and calcined at 600 °C in air. The properties of the catalysts were characterized and compared. Catalytic activities were examined for the vapor-phase double-bond isomerization of 1-butene at 150 °C and the liquid-phase Michael addition of 2-methylcyclohexane-1,3-dione to methyl vinyl ketone at room temperature. The properties of the modified ZrO2 i.e., basic site strength, were greatly affected by the ZrO2 precursors and the potassium modifiers. High yields of 2-butene with relatively high cis/trans ratios were found. Leaching of the potassium-modified ZrO2 makes the system less suitable for use in liquid-phase reactions.

8 citations

Journal ArticleDOI
TL;DR: A commercial Pd catalyst based on Sibunit carbon support was treated with H6TeO6 in a reducing media to obtain a Te coating on the surface of Pd particles as discussed by the authors.
Abstract: A commercial Pd catalyst based on Sibunit carbon support was treated with H6TeO6 in a reducing media to obtain a Te coating on the surface of Pd particles. The PdTe/C catalyst prepared in this way showed the ability to control the radical chain oxidation of 1,3-butadiene by promoting the selective formation of 2-butene-1,4-diol, 4-hydroxybut-2-enal and furan in DMA (total selectivity of 61% and yield of 7%). At the same time, the catalyst induced oxidation of 1,3-butadiene by a non-radical heterolytic mechanism involving the formation of two groups of primary products: (1) сrotonaldehyde and methyl vinyl ketone and (2) the products of oxygenation at the 1,4-positions. The compounds of the second group including 1,4-dimethoxy-2-butene and maleic acid dimethyl ester were formed on PdTe centers in MeOH. Increasing the Te concentration in the PdTe/C catalyst forced the conversion of 1,3-butadiene toward 1,4-oxygenation and simultaneously decreased the intensity of secondary oxidation, resulting in the selective formation of derivatives of the 1,4-oxygenation—1,4-dimethoxy-2-butene and allenic alcohol methyl ether (total selectivity of 84% and yield of 48%).

8 citations

Journal ArticleDOI
TL;DR: By condensation of acetone with 2-naphthylamine and 3-(4-fluorophenyl)-1H-pyrazole-4-, pyridine-3-, quinoline-2-carbaldehyde and 4-(2fluorobenzyloxy)benzaldehyde new 3-aryl(heteryl)1-methylbenzo[f]quinolines were synthesized.
Abstract: By condensation of acetone with 2-naphthylamine and 3-(4-fluorophenyl)-1H-pyrazole-4-, pyridine-3-, quinoline-2-, quinoline-6-carbaldehyde and 4-(2-fluorobenzyloxy)benzaldehyde new 3-aryl(heteryl)-1-methylbenzo[f]quinolines were synthesized. Reactions of acetone with 6-quinolylamine and aromatic aldehydes provided 3-aryl-1-methyl-4,7-phenanthrolines. Intermediate reaction products were isolated: 4-phenyl-or (3-pyridyl)-4-(2-naphthylamino or 6-quinolylamino)butan-2-ones.

8 citations

Journal ArticleDOI
TL;DR: In this paper, a photo-scissible poly(p-hydroxystyrene) derivatives with ketone groups was obtained by radical copolymerization of O-protected poly(HSt) and 2,2-diphenyl-4methylene-1,3-dioxorane (DPMD).
Abstract: INTRODUCTION Poly(p-hydroxystyrene) [poly(HSt)] and its derivatives are well known as functional polymers and have been applied variously to photoresist materials, composites, a physical gel, and a pH responsive material. Therefore, it is expected that endowing poly(HSt) derivatives with photo-scissibility will lead to the development of novel photosensitive functional materials. Recently, we have succeeded in the synthesis of photo-scissible poly(HSt) derivatives by the incorporation of ketone groups into the main chain, which was conducted by radical copolymerization of O-protected p-hydroxystyrene (ROSt) and 2,2-diphenyl-4methylene-1,3-dioxorane (DPMD) (Scheme 1). DPMD can undergo the radical ring-opening polymerization to afford the corresponding polyketone, which can be regarded as the copolymers of ethylene and carbon monoxide. Therefore, radical copolymerization of ROSt with DPMD and subsequent removal of protective groups gave the poly(HSt) derivatives having ketone groups in the main chain. The obtained poly(HSt) derivatives with ketone groups showed good photoscissibility based on Norrish-type reactions.

8 citations


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