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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: In this article, the reaction of (butadiene)zirconocene with hexacarbonyltungsten gives the metallacyclic (π-allyl) zirconoxy] carbene complex.
Abstract: The reaction of (butadiene)zirconocene with hexacarbonyltungsten gives the metallacyclic [(π-allyl)zirconoxy]carbene complex 7 This reagent adds to a variety of ketones to yield chiral nine-membered metallacyclic ring systems (8) These systems are thus formed by means of 1,4-selective coupling reactions of 1,3-butadiene with W(CO)6 and an organic carbonyl compound at the zirconocene template The ketones subjected to react with 7 include benzophenone, methyl vinyl ketone, cyclopentanone, and 3-methoxyestra-1,3,5(10)-trien-17-one (12) The coupling products of 7 with cyclopentanone (8c) and 12 (8d-A) were characterized by X-ray crystal structure analyses Of the four possible diastereomeric nine-membered metallacyclic coupling products of 7 with 12 a single isomer [8d-A with (13'S,17'R,2,3,4-pS) configuration] was formed with ≥98% selectivity and isolated in 95% yield Treatment of the complexes 8 in tetrahydrofuran with water and pyridine N-oxide very effectively removed both transition metals with the formation of the corresponding β,γ-unsaturated e-hydroxy carboxylic acids The overall reaction sequence has thus converted the steroid ketone 12 very selectively to 5-[3-methoxy-17β-hydroxyestra-1,3,5(10)-trien-17α-yl]-(E)-pent-3-enoic acid (10d)

14 citations

Journal ArticleDOI
TL;DR: Several strategies for the immobilization of a L-valine-derived auxiliary on a Merrifield resin and on poly(ethylene glycol) are reported in this article, where the latter is shown to work excellently in asymmetric copper(II)-catalyzed Michael reactions of cyclic β-oxo esters 2 with methyl vinyl ketone (4), yielding the corresponding addition products 5 with quaternary stereocenter in selectivities of 97-99

14 citations

Journal ArticleDOI
TL;DR: An asymmetric synthesis of orexin receptor antagonist MK-6096 piperidine core, ((3R,6R)-6-methylpiperidin-3-yl)methanol (3), is described in this paper.

14 citations

Journal ArticleDOI
TL;DR: In this paper, the authors investigated the Diels-Alder reaction between cyclopentadiene and methyl vinyl ketone in the presence and absence of the hydrogen-bonding catalysts thiourea and urea.
Abstract: The Diels–Alder reaction between cyclopentadiene and methyl vinyl ketone has been investigated by density functional calculations at the B3LYP/6-31+G* level, both in the absence and presence of the hydrogen-bonding catalysts thiourea and urea. The computed transition structures are concerted, but highly asynchronous in all cases. The addition of thiourea or urea accelerates the reaction and slightly changes the endo / exo selectivity. The activation barriers are lowered by 2–3 kcal/mol, while the activation free energies show smaller reductions due to unfavorable entropic effects. The addition of BF 3 causes a more pronounced decrease in the computed barriers by 8–11 kcal/mol. Despite their lower efficiency, hydrogen-bonding catalysts such as thiourea and urea may still offer an attractive alternative to Lewis acids because they do not suffer from product inhibition and can be used in aqueous solution.

14 citations

Journal ArticleDOI
TL;DR: In this article, the photodegradability properties of copolymers containing carbonyl group after UV irradiation were investigated and the results showed that the photooxidized copolymerization of styrene (St) and methyl vinyl ketone (MVK) was carried out in benzene by using azobisisobutylonitrile.
Abstract: The copolymerizations of styrene (St) and methyl vinyl ketone (MVK) or phenyl vinyl ketone (PVK) were carried out in benzene by using azobisisobutylonitrile (AIBN). The synthesized copolymers, poly(St-co-MVK) and poly(St-co-PVK), were identified by infrared (IR) spectroscopy. Under the presence of oxygen, the copolymers containing carbonyl group after UV irradiation showed photodegradable properties that caused by Norrish Type II reaction. The new IR characteristic peaks, such as carbonyl and vinyl groups of the photooxidized copolymers, increased by increasing UV irradiation time. In the photodegradation property, the color differences of the synthesized copolymers were higher than those of polystyrene with increasing UV irradiation time, which was caused by the inherent photodegradable property of carbonyl unit in copolymers. The average molecular weights of samples after UV irradiation for 300 h decreased, as compared with polymers before irradiation. © 1998 John Wiley & Sons, Inc. J Appl Polym Sci 67:1237–1242, 1998

14 citations


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