- Ruthenium-catalyzed hydrative dimerization of allenes
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Hydrative dimerization and hydration of allenes proceeded in the presence of a ruthenium catalyst and a strong acid such as trifluoroacetic acid. γ,δ-Unsaturated ketones and methyl ketones were isolated in moderate combined yields. No isomeric compound (isomeric enone) was isolated. Copyright
- Saito, Shinichi,Dobashi, Naotomo,Wakatsuki, Yasuo
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- Vinylic Organoboranes. 7. Stereoselective Synthesis of (E)-(1-Substituted-1-alkenyl)boronic Esters by the Nucleophilic Substitution of (Z)-(1-Bromo-1-alkenyl)boronic Esters with Organolithium or Grignard Reagents. Isolation and Oxidation to Ketones.
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The title compounds, (E)-R1CH=CR2B(OR)2 (4a-g), are prepared in a highly regio- and stereoselective manner by the reaction of (Z)-R1CH=CBrB(OR)2 (3a-g) with R2Li or R2MgX.The stereochemistry was established in two cases by isolating the E isomers 4 (R1, R2 = n-Bu; R1 = i-Pr, R2 = Me) in pure form and comparing the products with the corresponding Z isomers prepared by hydroboration of appropriate internal alkynes.Oxidation of 4 provides the corresponding ketones, R1CH2COR2, in high yields, confirming the carbon structures of the intermediate.As established previously, protonolysis of these (E)-boronic esters provides a synthesis of the pure (E)-alkenes.
- Brown, Herbert C.,Imai, Toshiro,Bhat, N. G.
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- Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution
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A kinetic resolution of tertiary nitroaldols derived from simple ketones is described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. By using a mixture of La-Li3-(1a)3 complex (LLB 2a) and La-Li3-(1b)3 (LLB* 2b) complex in a ratio of 2/1, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield. Copyright
- Tosaki, Shin-Ya,Hara, Keiichi,Gnanadesikan, Vijay,Morimoto, Hiroyuki,Harada, Shinji,Sugita, Mari,Yamagiwa, Noriyuki,Matsunaga, Shigeki,Shibasaki, Masakatsu
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- Iridium nanoparticles prepared in ionic liquids: An efficient catalytic system for the hydrogenation of ketones
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Ir(0) nanoparticles with 2.3 ± 0.4 nm in diameter prepared by simple reduction of [Ir(cod)Cl]2 in 1-n-butyl-3-methylimidazolium hexafluorophosphate ionic liquid constitute a simple, efficient and recyclable catalytic system for the solventless or biphasic hydrogenation of ketones under mild reaction conditions.
- Fonseca, Gledison S.,Scholten, Jackson D.,Dupont, Jairton
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- Palladium/Copper-catalyzed Oxidation of Aliphatic Terminal Alkenes to Aldehydes Assisted by p-Benzoquinone
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The development of an anti-Markovnikov Wacker-type oxidation for simple aliphatic alkenes is a significant challenge. Herein, a variety of aldehydes can be selectively obtained from various unbiased aliphatic terminal alkenes using PdCl2(MeCN)2/CuCl in the presence of p-benzoquinone (BQ) under mild reaction conditions. Isomerization of the terminal alkene to the internal alkene was suppressed via slow addition of the starting material to the reaction mixture. In addition to the Pd catalyst, CuCl and BQ were essential in order to obtain the anti-Markovnikov product with high selectivity. Terminal alkenes bearing a halogen substituent afforded their corresponding aldehydes with high anti-Markovnikov selectivity. The halogen acts as a directing group in the reaction. DFT calculations indicate that a μ-chloro Pd(II)?Cu(I) bimetallic species with BQ coordinated to Cu is the catalytically active species in the case of a terminal alkene without a directing group.
- Komori, Saki,Yamaguchi, Yoshiko,Murakami, Yuka,Kataoka, Yasutaka,Ura, Yasuyuki
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- A route for lignin and bio-oil conversion: Dehydroxylation of phenols into arenes by catalytic tandem reactions
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Finding a workaround: The conversion of lignin into low-boiling-point arenes instead of high-boiling-point phenols could greatly facilitate conventional refinery processes. A new procedure for the depolymerization of lignin and simultaneous conversion phenols into arenes is described. The method can also be rendered as a fundamental finding for the upgrade of bio-oils to arenes under mild conditions. Copyright
- Wang, Xingyu,Rinaldi, Roberto
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- Highly efficient methyl ketone synthesis by water-assisted C-C coupling between olefins and photoactivated acetone
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(Chemical Equation Presented) Photoirradiation of an acetone/water mixture containing olefins affords the corresponding methyl ketones highly efficiently via a water-assisted CsC coupling between acetonyl radical and olefins.
- Shiraishi, Yasuhiro,Tsukamoto, Daijiro,Hirai, Takayuki
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- Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution
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Full details of the kinetic resolution of tertiary nitroaldols derived from simple ketones are described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. Using
- Hara, Keiichi,Tosaki, Shin-ya,Gnanadesikan, Vijay,Morimoto, Hiroyuki,Harada, Shinji,Sugita, Mari,Yamagiwa, Noriyuki,Matsunaga, Shigeki,Shibasaki, Masakatsu
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Read Online
- Metal complex, electroluminescent device containing metal complex and application of metal complex
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The invention provides a metal complex, an electroluminescent device containing the metal complex and application of the electroluminescent device, the metal complex has an M(La)m(Lb)n structure, the metal complex provided by the invention can more effectively finely adjust the luminescence color and adjust the luminescence peak width, so that the half-peak width is narrowed, the luminescence color is more saturated, the device efficiency is improved, and the current efficiency and the external quantum efficiency are relatively high.
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Paragraph 0154; 0158-0160
(2021/07/17)
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- Preparation method of cyclohexyl acetone
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The invention provides a preparation method of cyclohexyl acetone, and particularly relates to the preparation method of cyclohexyl acetone by reacting a first catalyst, a second catalyst, cyclohexene and acetone with a mixed gas containing nitrogen and oxygen in acetic acid. The method disclosed by the invention is simple to operate, mild in reaction condition, less in generated solid waste, simple in post-treatment, recyclable in solvent and suitable for industrial production, and a reaction reagent with relatively high toxicity is avoided.
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Paragraph 0009; 0041-0062
(2021/05/29)
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- Preparation method of (cyclic)alkyl acetone
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A purpose of the invention is to provide a preparation method of (cyclic)alkyl acetone. The preparation method specifically comprises: sequentially adding acetic acid, potassium acetate, manganese acetate, acetic anhydride and acetone into a reaction flask, heating to a reaction temperature, adding olefin and an oxidant, and carrying out a free radical addition reaction represented by the following formula 2 at a reaction temperature of 30-100 DEG C to obtain (cyclic) alkyl acetone represented by a formula 2. According to the present invention, the preparation method is simple and safe to operate, and low in production cost.
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Paragraph 0019-0022
(2020/01/08)
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- NHC-stabilised Rh nanoparticles: Surface study and application in the catalytic hydrogenation of aromatic substrates
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New Rh-NPs stabilised by N-Heterocyclic Carbenes (NHC) were synthesized by decomposition of [Rh(η3-C3H5)3] under H2 atmosphere and fully characterized. Surface studies by FT-IR and NMR spectroscopy employing isotopically labelled ligands were also performed. The Rh0.2 NPs are active catalysts in the reduction of various aromatic substrates. In the reduction of phenol, high selectivities to cyclohexanone or cyclohexanol were obtained depending on the reaction conditions. However, this catalytic system exhibited much lower activity in the hydrogenation of substituted phenols. Pyridine was easily hydrogenated under mild conditions and interestingly, the hydrogenation of 4-methyl and 4-trifluoromethylpyridine resulted slower than that of 2-methylpyridine. The hydrogenation of 1-(pyridin-2-yl)propan-2-one provided the β-enaminone 13a in high yield as a consequence of the partial reduction of the pyridine ring followed by isomerization. Quinoline could be either partially hydrogenated to 1,2,3,4-tetrahydroquinoline or fully reduced to decahydroquinoline by adjusting the reaction conditions.
- Martinez-Espinar, Francisco,Blondeau, Pascal,Nolis, Pau,Chaudret, Bruno,Claver, Carmen,Castillón, Sergio,Godard, Cyril
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p. 113 - 127
(2017/09/08)
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- An alkylidene carbene C-H activation approach toward the enantioselective syntheses of spirolactams: Application to the synthesis of (-)-adalinine
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A method based on in situ alkylidene carbene generation-C-H insertion reaction of 5-(3-oxobutyl)pyrrolidin-2-ones and 6-(3-oxobutyl)piperidin-2-ones is developed for the enantioselective synthesis of 1-azaspiro[4,4]non-6-ene-2-ones and 6-azaspiro[4,5]dec-1-ene-7-ones. The required 5-(3-oxobutyl)pyrrolidin-2-ones and 6-(3-oxobutyl)piperidin-2-ones are prepared from the Wacker oxidation of internal alkenes typified by 5-(but-2-enyl)pyrrolidin-2-ones and 6-(but-2-enyl)piperidin-2-ones, respectively. Excellent regioselectivity (≥92:8) is realized for the Wacker oxidation, and high yields (78-89%) of the desired lactam ketones are obtained. The results from further investigations into the Wacker oxidation suggested that the high regioselectivity of the oxidation in these lactam alkenes might be due to the participation of the lactam nitrogen via intramolecular coordination to Pd(II) during the reaction. Studies on alkylidene carbene generation-C-H insertion reaction of the lactam ketones revealed that the reaction efficiency is sensitive to the reaction temperature and the amount of lithio(trimethylsilyl)diazomethane employed, which led to the development of optimal reaction conditions for effecting alkylidene carbene generation-C-H insertion. Using the optimal reaction conditions, good to high yields (53-76%) of both γ- and δ-lactam spirocycles were obtained. The synthetic utility of the spirolactams was demonstrated by the synthesis of (-)-adalinine.
- Annadi, Krishna,Wee, Andrew G. H.
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supporting information
p. 1021 - 1038
(2016/02/19)
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- Tuning the selectivity in the hydrogenation of aromatic ketones catalyzed by similar ruthenium and rhodium nanoparticles
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Ru and Rh nanoparticles (NPs) RuI, RuII, RhI and RhII, stabilised by triphenylphosphine (PPh3) and diphenylphosphinobutane (dppb) were synthesised, characterised and applied as catalysts in the hydrogenation of several aromatic ketones. The effects of the nature of the metal and of the stabilising agent on the aryl versus ketone hydrogenation were studied. For RhNPs, the coordination of arene dominates the interaction of the substrate with the NP, whereas the coordination of the ketone group was not evidenced. For RuNPs, however, the results show that both arene and ketone coordinate to the NPs surface in a competitive manner. The properties of the stabilising ligands have a clear influence on the outcome of the reaction, and for the Rh-catalysed reactions, products of hydrogenolysis were only formed if PPh3 was used as the stabiliser. The structure of the substrate was also a key factor for the selectivity.
- Castelbou, Jessica Llop,Bres-Femenia, Emma,Blondeau, Pascal,Chaudret, Bruno,Castilln, Sergio,Claver, Carmen,Godard, Cyril
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p. 3160 - 3168
(2015/02/19)
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- ALDEHYDE-SELECTIVE WACKER-TYPE OXIDATION OF UNBIASED ALKENES
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This disclosure is directed to methods of preparing organic aldehydes, each method comprising contacting a terminal olefin with an oxidizing mixture comprising: (a) a dichloro-palladium complex; (b) a copper complex; (c) a source of nitrite; under aerobic reaction conditions sufficient to convert at least a portion of the terminal olefin to an aldehyde.
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Page/Page column 0140-0149; 0155-0164; 0166-0168; 0175
(2014/10/29)
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- Aldehyde-selective wacker-type oxidation of unbiased alkenes enabled by a nitrite co-catalyst
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Breaking the rules: Reversal of the high Markovnikov selectivity of Wacker-type oxidations was accomplished using a nitrite co-catalyst. Unbiased aliphatic alkenes can be oxidized with high yield and aldehyde selectivity, and several functional groups are tolerated. 18O-labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt. Copyright
- Wickens, Zachary K.,Morandi, Bill,Grubbs, Robert H.
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supporting information
p. 11257 - 11260
(2013/11/06)
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- Terminal olefins to linear α,β-unsaturated ketones: Pd(II)/hypervalent iodine co-catalyzed wacker oxidation-dehydrogenation
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Development of a mild (35 C, no Bronsted acids) tandem Wacker oxidation-dehydrogenation of terminal olefins was accomplished using palladium(II) and hypervalent iodine co-catalysis. The reaction affords linear aryl and alkyl α,β-unsaturated ketones directly from readily available terminal olefins in good yields (average 75% per step) with excellent functional group tolerance and chemo- and stereoselectivities. The hypervalent iodine co-catalyst was found to be critical for dehydrogenation but was not effective as a stoichiometric oxidant.
- Bigi, Marinus A.,White, M. Christina
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supporting information
p. 7831 - 7834
(2013/07/19)
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- NHC-stabilized ruthenium nanoparticles as new catalysts for the hydrogenation of aromatics
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The application of ruthenium nanoparticles (RuNPs) stabilized by the N-heterocyclic carbenes (NHC) N,N′-di(tert-butyl)imidazol-2-ylidene (ItBu) and 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene IPr as catalysts in the hydrogenation of several substrates is reported under various reaction conditions (solvent, substrate concentration, substrate/metal ratio, temperature). The RuNHC nanoparticles are active catalysts in the hydrogenation of aromatics and show an interesting ligand effect, RuIPr NPs being generally more active than RuItBu. The Royal Society of Chemistry 2013.
- Gonzalez-Galvez, David,Lara, Patricia,Rivada-Wheelaghan, Orestes,Conejero, Salvador,Chaudret, Bruno,Philippot, Karine,Van Leeuwen, Piet W.N.M.
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- Efficient silver-free gold(I)-catalyzed hydration of alkynes at low catalyst loading
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The use of [(IPr)AuOH] as versatile, air- and moisture-stable pre-catalyst permits the in situ generation of the cationic gold(I) species [(IPr)Au]X after reaction with a Br?nsted acid. This catalytic system presents as a main advantage the lack of use of a silver salt activator or co-catalyst which is often air-, light- and moisture-sensitive. A general gold(I)-catalyzed procedure using this in situ activation at very low catalyst loading is reported for the hydration of a broad range of internal and terminal alkynes.
- Nun, Pierrick,Ramón, Rubén S.,Gaillard, Sylvain,Nolan, Steven P.
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experimental part
p. 7 - 11
(2011/02/17)
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- Cyanocuprates convert carboxylic acids directly into ketones
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Carboxylic acids were converted directly in 56-99% yields into methyl, n-butyl, and isopropyl ketones using excess cyanocuprates R2CuLi 3 LiCN. A substrate with a stereocenter α to the carboxylic acid was converted into ketones with very little loss of enantiomeric purity. A variety of functional groups were tolerated including aryl bromides. This direct transformation of a carboxylic acid into ketone with minimal tertiary alcohol formation is proposed to involve a relatively stable copper ketal tetrahedral intermediate.
- Genna, Douglas T.,Posner, Gary H.
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supporting information; experimental part
p. 5358 - 5361
(2011/12/15)
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- Hydroboration with pyridine borane at room temperature
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Treatment of pyridine borane (Py·BH3) with iodine, bromine, or strong acids affords activated Py·BH2X complexes that are capable of hydroborating alkenes at room temperature. Evidence is presented for an unusual hydroboration mechanism involving leaving group displacement. In contrast to THF·BH3, hydroboration with Py·BH2I selectively affords the monoadducts. The crude hydroboration products are converted into synthetically useful potassium alkyltrifluoroborate salts upon treatment with methanolic KHF2. Copyright
- Clay, Julia M.,Vedejs, Edwin
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p. 5766 - 5767
(2007/10/03)
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- Preferential catalytic hydrogenation of aromatic compounds versus ketones with a palladium substituted polyoxometalate as pre-catalyst
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A palladium-substituted polyoxometalate having a Keggin structure, supported on γ-alumina or active carbon, was used as a catalyst precursor for catalytic hydrogenation. The catalyst system enabled fast hydrogenation of arenes at 30 bar H2 and 230°C. Most interesting was the finding that arenes could be selectively reduced in the presence of distal ketone groups under similar conditions, 30 bar H2 and 200°C. For example, 1-phenyl-2-propanone yielded 1-cyclohexyl-2-propanone with no reduction of the ketone moiety. Additionally, aromatic compounds with vicinal (conjugated) ketone moieties underwent complete hydrogenation to saturated hydrocarbons and catalytic McMurry coupling was observed for aliphatic aldehydes.
- Kogan, Vladimir,Aizenshtat, Zeev,Neumann, Ronny
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p. 272 - 274
(2007/10/03)
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- Multicomponent reactions involving 2-methyleneaziridines: Rapid synthesis of 1,3-disubstituted propanones
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Ring opening of 1-alkyl-2-methyleneaziridines 1 or 2 is accomplished with organocopper reagents (R2CuLi or RMgX/CuI) in the presence of boron trifluoride diethyl etherate giving 1-substituted propan-2-ones 3-9 in 42-88% yield. Ring opening with RMgC1/CuI in the absence of the Lewis acid allows further alkylation of the metalloenamine (metalated imine) intermediate in a regiocontrolled manner. The sequential formation of two new intermolecular carbon-carbon bonds in this reaction provides a rapid entry into a variety of 1,3-disubstituted propan-2-ones, including 11 and 14-23. The scope and mechanism of this multicomponent reaction (MCR) has been assessed. It is established that this MCR tolerates alkyl, aryl, and benzyiic Grignard reagents and a wide range of electrophiles, including alkyl iodides, bromides, and tosylates, as well as epoxides and aldehydes. In addition, gem-dimethyl substitution on the exocyclic double bond of the 2-methyleneaziridine is tolerated. This MCR has been applied to the one-pot synthesis of (Z)-6-heneicosen11-one, 25, an important sex attractant of the Tussock moth. Using 3-deuterio-1-(1-phenylethyl)2-methyleneaziridine, 26, we determined that this MCR occurs predominantly by direct ring opening at the sp3-hybridized aziridine carbon atom (C-3).
- Hayes, Jerome F.,Shipman, Michael,Twin, Heather
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p. 935 - 942
(2007/10/03)
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- Generation of metalloenamines by carbon-carbon bond formation: Ring opening reactions of 2-methyleneaziridines with organometallic reagents
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Ring opening of 2-methyleneaziridines with Grignard reagents in the presence of CuI yields metalloenamines in a regiospecific fashion which can be further reacted with electrophiles to produce functionalised ketones via a one-pot process.
- Hayes,Shipman,Twin
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p. 1791 - 1792
(2007/10/03)
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- Potassium Permanganate-Mediated Radical Reactions: Chemoselective Addition of Acetone to Olefins
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A practical and efficient protocol for the radical addition of acetone (1) to olefins 2a-d, mediated by potassium permanganate, has been developed.The in situ generation of manganese(III) allows the chemoselective synthesis of saturated C-C bond formation products 4a-d in 39-58percent yield.Furthermore, the required amount of manganese is reduced drastically in account of the catalytic reaction cycle.
- Linker, Ursula,Kersten, Berthold,Linker, Torsten
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p. 9917 - 9926
(2007/10/02)
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- Selective homologation of ketones and aldehydes with diazoalkanes promoted by organoaluminum reagents
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Organoaluminum-promoted single homologation or ring expansion of ketones and aldehydes with diazoalkanes has been described, and among various organoaluminium reagents, exceptionally bulky methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) is found to be highly effective for the selective homologation of various ketones and aldehydes.
- Maruoka,Concepcion,Yamamoto
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p. 1283 - 1290
(2007/10/02)
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- THE INVENTION OF NEW RADICAL CHAIN REACTIONS. PART X. HIGH YIELD RADICAL ADDITION REACTIONS OF αβ-UNSATURATED NITROOLEFINS. AN EXPEDIENT CONSTRUCTION OF THE 25-HYDROXY-VITAMIN D3 SIDE CHAIN FROM BILE ACIDS.
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Radicals derived from thiohydroxamic esters 3 readily add to nitroolefins 5 (Z=NO2) to give good yields of α-nitrosulphides.These adducts, where the structure permits, are easily oxidised to carboxylic acids 8 by treatment with alkaline hydrogen peroxide.Reductive cleavage to the corresponding aldehydes or ketones 9 is efficiently carried out by the action of TiCl3.Addition of methyl magnesium iodide to methyl ketone derived from 3α-acetoxy 11-oxo cholanic acid gives steroid 10 possessing the 25-hydroxycholesterol side chain of the vitamin D3 metabolites.Radical additions to 1-phenylthio-2-nitropropene 11 have been briefly studied.
- Barton, Derek H.R.,Togo, Hideo,Zard, Samir Z.
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p. 5507 - 5516
(2007/10/02)
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- Reactions radicalaires du percarbonate de O,O-tert-butyle et O-isopropenyle: acetonylations assistees par un co-amorceur
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By decomposition in alkanes, ethers, ketones, acids, esters and nitriles of equimolecular mixtures of O,O-tert-butyl and O-isopropenyl peroxicarbonate and tert-butyl peroxyacetate, the "assisted" acetonylation of the solvents has been accomplished.The presence of the co-initiator allows the yield of the free radical acetonylation to be markedly improved: the formation of the by-product acetonylacetone is avoided and the yield of acetonylated derivatives is strongly enhanced while the regioselectivity of the processes is preserved and even increased in some cases.
- Jaouhari, Rabih,Filliatre, Claude,Villenave, Jean-Jacques
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p. 2295 - 2298
(2007/10/02)
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- 1-BROMO-1-(TRIMETHYLSILYL)-1-ALKENES. A SINGLE SYNTHON FOR BOTH THE CARBONYL ANION AND CATION
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The utility of 1-bromo-1-(trimethylsilyl)-1-alkenes as a single synthon for both the carbonyl anion and cation is demonstrated.
- Miller, R. B.,Al-Hassan, M. I.,McGarvey, G.
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p. 969 - 976
(2007/10/02)
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- DECOMPOSITION DU PERCARBONATE DE O,O-t-BUTYLE ET O-ISOPROPENYLE EN SOLUTION DANS DES CYCLANES
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Thermolysis of O,O-t-butyl and O-isopropenyl percarbonate in cyclohexane involves free-radical acetonylation of solvent.Free radicals derived from solvent add to the percarbonate double bond and after a double β-scission reaction, cyclohexylacetone carbon dioxide and t-butoxy radicals are formed.Abstracting H atoms from the solvent, t-butoxy radicals regenerate free radicals from solvent, and the reaction becomes a chain process.Extending the study to other cycloalkanes it has been shown that the process is a general synthesis method for cycloalkylacetones.On the other hand, competitive reactions of pairs of solvents have shown that the reactivity of the substrates depends on H atom lability and on more complex phenomena like transfers between hydrocarbons and C-centred free-radicals.
- Jaouhari, R.,Filliatre, C.,Maillard, B.,Villenave, J.J.
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p. 3137 - 3142
(2007/10/02)
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- Synthesis and pharmacological study of diphenylalkylamines with cycloaliphatic residues; new coronary vasodilators
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The paper describes the synthesis and the pharmacological evaluation of some derivatives of prenylamine, all with a cycloaliphatic ring within or instead of the isopropylamine moiety. Where the alicyclic ring had a bulky substituent in para were more active than prenylamine as coronary vasodilators on isolated guinea pig heart (Langendorff). The most interesting derivative was MG 8926 [N (3,3 diphenylpropyl) α methyl β cyclohexylethylamine], which was more active than prenylamine on Langendorff's heart and in enhancing the pressor response to catecholamines and inhibiting the isoprenaline induced hypotension. Moreover, it had almost the same effects as prenylamine as spasmolytic, local and general anesthetic, on heart rate and arterial pressure and against coronary spasm from pitressin.
- Carenini,Carissimi,Gentili,Grumelli,Picciola,Ravenna
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p. 2127 - 2136
(2007/10/06)
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