Showing papers on "Methyl vinyl ketone published in 1989"
TL;DR: In this article, the gas phase reaction of methyl vinyl ketone with the OH radical, in the presence of NOx, was investigated at 298 ± 2 K and atmospheric pressure of air.
Abstract: The gas-phase reaction of methyl vinyl ketone with the OH radical, in the presence of NOx, was investigated at 298 ± 2 K and atmospheric pressure of air. Glycolaldehyde and methylglyoxal were observed to be the major products, with a combined yield of 0.89 ± 0.16. The sum of the yields of the two other main products, formaldehyde and peroxyacetyl nitrate, were found to be essentially unity. The product yield data for glycolaldehyde and methylglyoxal indicate that OH radical addition to the terminal carbon atom of the >CC< bond accounts for 72 ± 21% of the overall reaction, with the remaining 28 ± 9% proceeding via addition to the inner carbon atom of the double bond.
124 citations
TL;DR: In this paper, the Diels-Alder reactions of cyclopentadiene with methyl acrylate and methyl vinyl ketone were improved by using ethylammonium nitrate.
114 citations
TL;DR: In this article, a cycloaddition reaction of ethyl 2-(benzenesulfonylmethyl)-2-propenyl carbonate with methyl acrylate and methyl vinyl ketone in the presence of a chiral ferrocenylphosphine-palladium catalyst gave optically active methylenecyclopentane derivatives of up to 78% ee.
59 citations
TL;DR: Diethyl ketomalonate reacts fast with acrylic acid esters, acrylonitrile and methyl vinyl ketone under the catalytic influence of 1,4-diazabicyclo(2.2) octane (DABCO) to provide the corresponding multifunctional molecules.
21 citations
TL;DR: In this paper, the authors described a number of useful radical reactions mediated by Et3B, such as the radical addition of R3SnH to acetylenes and its application to cyclization reaction, the addition of Ph3GeH to Acetylenes, and the reduction of dithiocarbonates with n-Bu3snH-Et3B.
Abstract: Synthetically useful radical reactions mediated by Et3B are described. An addition of catalytic amount of Et3B to a solution of triphenylstannane, triphenylgermane, or benzenethiol in toluene promotes the effective formation of the corresponding triphenylstannyl, triphenylgermyl, or benzenethiyl radical, respectively. Topics are (1) Et3B induced radical addition of R3SnH to acetylenes and its application to cyclization reaction, (2) Et3B induced stereoselective radical addition of Ph3GeH to acetylenes and its application to isomerization of olefins, (3) Et3B induced radical addition of thiols to acetylenes, (4) A facile reduction of dithiocarbonates with n-Bu3SnH-Et3B, (5) Et3B induced hydrodehalogenation of organic halides by tin hydrides, and (6) Et3B-mediated Reformatsky type reaction and three component coupling reaction of alkyl iodides, methyl vinyl ketone, and carbonyl compounds.
21 citations
TL;DR: In this paper, the Nef reaction was used for the synthesis of jasmone, methyl jasmonate, and γ-jasmolactone, three jasmin constituents.
20 citations
TL;DR: In this article, collisional activation decomposition (CAD) combined with tandem mass spectrometry (MS/MS) and also Fourier transform mass spectroscopy (FTMS) was used to investigate the structure of the 1,3-butadiene radical cation.
Abstract: The 1,3-butadiene radical cation reacts with acrolein and methyl vinyl ketone to produce ‘stable’ adducts. The nature of the reaction and the structures of the adducts were investigated by collisional activation decomposition (CAD) combined with tandem mass spectrometry (MS/MS), and also by Fourier transform mass spectrometry. The CAD spectra of gas-phase adducts were compared with those of suitable model compounds. On that basis, it was determined that the 1,3-butadiene radical cation undergoes a cycloaddition with these α,β-unsaturated carbonyl compounds. The butadiene radical cation serves as the ‘ene’, and the acrolein and methyl vinyl ketone react as dienes, forming cycloadducts having 2-ethenyl-2,3-dihydropyran radical cation structures.
15 citations
TL;DR: In this paper, an efficient synthesis of substituted cyclobutanes via Ti(IV) catalyzed 2+2 cycloadditions of methoxymethyl vinyl ketone with alkenes was reported.
13 citations
TL;DR: Chloro[2,3-η-(methyl propenoate)copper(I) has been determined from single-crystal X-ray diffraction data recorded at −105°C as discussed by the authors.
9 citations
TL;DR: In this paper, the macromolecular metal chelates (MMCs) were synthesized via the interaction of macromolescular ligands with TiCl4, Ti(OC4H9)9)4, Ni(OCOCH3)2, CoCl2 and Co( OCOCH3), and it was shown that MMC formed from aluminium organic compounds provided efficient catalysts for polymerization processes.
9 citations
Journal Article•
TL;DR: Reaction of pyrazole and 3,5-dimethylpyrazole with methyl vinyl ketone gave 4-(1H-pyrazol-1-yl)-2-butanones which were converted to N-substituted 4-( 1H- pyrazol -2-butylamines by reductive amination using ammonium acetate, primary or secondary amines and sodium cyanoborohydride as reducing agent.
Abstract: Reaction of pyrazole and 3,5-dimethylpyrazole with methyl vinyl ketone gave 4-(1H-pyrazol-1-yl)-2-butanones which were converted to N-substituted 4-(1H-pyrazol-1-yl)-2-butylamines by reductive amination using ammonium acetate, primary or secondary amines and sodium cyanoborohydride as reducing agent. These new pyrazole derivatives were found to have an inhibitory effect on platelet aggregation in vitro.
TL;DR: The first representatives of 5-hydroxyisoxazolidines with the residue of an aliphatic carboxylic acid attached to the nitrogen atom were obtained by acylation of 5 -hydroxy-3,3,5-trimethylisoxozolidine as mentioned in this paper.
Abstract: The reaction of methyl vinyl ketone with N-Phenyl-hydroxylamine leads to a tautomeric mixture of 5-hydroxy-2-phenyl-5-methylisoxazolidine and its linear form, while the reaction with benzohydroxamic acid leads to linear products of addition to the oxygen or nitrogen atoms, depending on the reaction conditions. The first representatives of 5-hydroxyisoxazolidines with the residue of an aliphatic carboxylic acid attached to the nitrogen atom were obtained by acylation of 5-hydroxy-3,3,5-trimethylisoxazolidine.
TL;DR: The Diels-Alder reaction of 3-acetoxy-1-vinylcyclohexene (1c) with methyl vinyl ketone (MVK) at 110 and 150°C gave predominantly the adducts 1-acetox-8-acetyl-8aβH-4a(5)-octalin, 3b (8βH) and 3a (8αH), respectively, along with other minor Adducts.
Abstract: The Diels-Alder reaction of 3-acetoxy-1-vinylcyclohexene (1c) with methyl vinyl ketone (MVK) at 110 and 150°C gave predominantly the adducts 1-acetoxy-8-acetyl-8aβH-4a(5)-octalin, 3b (8βH) and 3a (8αH), respectively, along with other minor adducts. The stereochemistry of 3a was independently confirmed by X-ray crystallographic analysis of the p-bromobenzoate (3e) derived from 1-desacetyl-3a(3d). The predominant approach of the dienophile (MVK) to 1c was found to have occurred anti to the allylic acetate group, contrary to the empirical rule proposed recently.
TL;DR: In this article, the reactions of lithiated 1-(t-butylsulfinyl)prop-2-ene with methyl crotonate, mesityl oxide and crotonaldehyde gave largely carbonyl addition products arising from reaction through C1 or C3 of the allyl system.
Abstract: The reactions of lithiated 1-(t-butylsulfinyl)prop-2-ene, 1-(t-butylsulfinyl)-3-methylbut-2-ene, 1-(t-butylsulfinyl)but-2-ene, 1-(phenylsulfinyl)but-2-ene and 2-methyl-1-(phenylsu1finyl)prop- 2-ene with methyl vinyl ketone, mesityl oxide and crotonaldehyde give largely carbonyl addition products arising from reaction through C1 or C3 of the allyl system. In the case of methyl crotonate, conjugate addition through C3 is observed. The initially formed diastereomers of the C1 adducts, allylic sulfoxides, are configurationally unstable. Only the lithiated 1-(t-butylsulfinyl)-3-methylbut-2-ene undergoes conjugate addition with methyl vinyl ketone to give an (E)-vinyl sulfoxide whose formation may involve the trans-decalyl transition state characteristic of the reactions of lithiated allylic sulfoxides with cyclic enones.
Patent•
06 Feb 1989
TL;DR: In this paper, an insoluble and non-corrosive cation exchange polymer was used as a catalyst to obtain 4-(4- hydroxyphenyl)-2-butanone.
Abstract: PURPOSE:To industrially and advantageously obtain the titled compound which is an aromatic component of raspberry and useful as a perfume, by reacting phenol with methyl vinyl ketone using an insoluble and noncorrosive cation exchange polymer as a catalyst. CONSTITUTION:Phenol in an excessive amount is reacted with methyl vinyl ketone, preferably at 40-70 deg.C using a cation exchange polymer (especially preferably having sulfonic acid groups) as a catalyst to afford 4-(4- hydroxyphenyl)-2-butanone. Separation of the catalyst after the reaction is facilitated and the catalyst can be reused by using the cation exchange polymer as the catalyst without requiring a highly corrosion-resistant reactor. Furthermore, this method is improved in economic efficiency without requiring removal of water in the raw materials.
TL;DR: In this article, copolymerization of ethylcyanoacrylate with methyl vinyl ketone (mvk, M2) was studied and the Fineman-Ross method was used.
TL;DR: In this article, it was shown on the example of 1-hydroxy-5-methyltetrazole with methyl vinyl ketone that N-hydroxtetrazoles attach to substances with activated multiple bonds.
Abstract: 1.
It was shown on the example of the reaction of 1-hydroxy-5-methyltetrazole with methyl vinyl ketone that N-hydroxytetrazoles attach to substances with activated multiple bonds. The addition products are solely the products of N(3 and 4)-γ-oxoalkylation.
2.
Upon heating, 3- and 4-γ-oxoalkylated 1-oxides of tetrazoles are in a tautomeric equilibrium.
TL;DR: In this paper, a cycloaddition reaction of ethyl 2-(benzenesulfonylmethyl)-2-propenyl carbonate with methyl acrylate and methyl vinyl ketone in the presence of a chiral ferrocenylphosphine-palladium catalyst gave optically active methylenecyclopentane derivatives of up to 78% ee.
Abstract: Cycloaddition reaction of ethyl 2-(benzenesulfonylmethyl)-2-propenyl carbonate with methyl acrylate and methyl vinyl ketone in the presence of a chiral ferrocenylphosphine-palladium catalyst gave optically active methylenecyclopentane derivatives of up to 78% ee.
TL;DR: In this paper, a 30-40% selectivity was achieved by the reaction of methanol and acetone at 350 °C over Ti(IV)-, Cr(III)-, Mn(II)-, and Sn(IV) exchanged forms of fluoro tetrasilicic mica (TSM).
Abstract: Methyl vinyl ketone was obtained at 30–40% selectivity by the reaction of methanol and acetone at 350 °C over Ti(IV)-, Cr(III)-, Mn(II)-, and Sn(IV)-exchanged forms of fluoro tetrasilicic mica (TSM). The addition of oxygen into the feed increased the conversion of acetone and the reaction over Ti(IV)-TSM converted 11% of acetone fed into methyl vinyl ketone at 85% selectivity.
TL;DR: In this paper, the Diels-Alder reactions of cyclopentadiene with methyl acrylate and methyl vinyl ketone were improved by using ethylammonium nitrate.
Abstract: Relative to nonpolar organic solvents, ethylammonium nitrate gave endo stereoselectivity enhancements for the Diels-Alder reactions of cyclopentadiene with methyl acrylate and methyl vinyl ketone.
TL;DR: In this article, the authors investigated the kinetics of anionic homopolymerization of methyl vinyl ketone (MVK) and acrylamide (AAm) under argon in the presence of an initiating adduct.
Abstract: N-(Butyl-3-one)imidazole acts as an initiating adduct which is formed in the anionic polymerization of methyl vinyl ketone (MVK) induced by imidazole (Im) and is directly formed from Im and the MVK monomer. The kinetics of the anionic homopolymerization of MVK and acrylamide (AAm) under argon in the presence of the adduct were investigated in tetrahydrofuran (THF). The rate of polymerization for the MVK system is expressed as Rp = k[Adduct] [MVK], where k = 3.1 × 10−6 L/(mol·s)in THF at 30°C. The overall activation energy, Ea , was found to be 5.34 kcal/mol. The Rp for the AAm system is expressed as Rp = k[Adduct] [AAm], where k = 6.8 × 10−6 L/(mol·s) in THF at 30°C, with Ea 7.78 kcal/mol. The mechanism of the polymerization induced by the initiator adduct is discussed on the basis of these results.
TL;DR: In this article, the Nef reaction was used for the synthesis of jasmone, methyl jasmonate, and γ-jasmolactone, three jasmin constituents.
Abstract: (Z)-7-Nitro-3-heptene is used as central intermediate in the synthesis of jasmone (13), methyl jasmonate (15), and γ-jasmolactone (16), three jasmin constituents. Conjugate addition of the title nitro compound, by heterogeneous catalysis, to methyl vinyl ketone, or acrolein, or methyl acrylate, followed by Nef reaction, affords (Z)-undec-8-ene-2,5-dione, (Z)-1,4-dioxodec-7-ene, and (Z)-4-oxo-dec-7-enoic acid methyl ester respectively, which are easily converted into jasmone, methyl jasmonate and γ -jasmolactone.
01 Jan 1989
TL;DR: In this article, the authors show that metabolic stereospecificity manifests itself in macroscopic chiral structures such as snail shells, in which high stereoselectivities are observed.
Abstract: Metabolism in man, animal and plant uses optically active compounds, e.g. L-amino acids, D-sugars etc. This metabolic stereospecificity manifests itself in macroscopic chiral structures such as snail shells, in which high stereoselectivities are observed. Other examples for plants are shown in Fig. 1.