19766-36-0Relevant academic research and scientific papers
Michael reactions promoted by η1-O-enolatoruthenium(II) complexes derived from Ru(cod)(cot), diphosphine, and dimethyl malonate
Alvarez, Salvador G.,Hasegawa, Sachi,Hirano, Masafumi,Komiya, Sanshiro
, p. 5209 - 5212 (1998)
The Michael reaction of 1,3-dicarbonyls with α,β-unsaturated esters and nitriles has been carried out very efficiently, under mild and neutral conditions, in the presence of a catalytic amount of trans-hydrido(η1-O- enolato) ruthenium(II) complex (2), which is prepared from the reaction of Ru(cod)(cot) (1) (cod = cycloocta-1,5-diene; cot = cycloocta-1,3,5-triene) with dimethyl malonate in the presence of 1,2-bis(diphenylphosphino)ethane (dpe).
POLYVALENT ESTER COMPOSITION AND MANUFACTURING METHOD THEREFOR
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Paragraph 0044, (2017/06/02)
PROBLEM TO BE SOLVED: To provide a composition having high compatibility with an acryl resin, capable of improving bending property when used for an acryl resin film, excellent in handleability, less in breed out, having nonvolatility or low volatility, environmentally friendly and capable of being used as a plasticizer. SOLUTION: There is provided a polyvalent ester composition containing a compound represented by the formula (1) and having percentage of a compound where total of x and y is 3 of 30 to 99 mol% based on 100 mol% of the compound represented by the formula (1), the polyvalent ester compound and a manufacturing method therefor including a process of reacting acrylic acid ester, an active methylene compound and methylene glutaric acid diester. In general formula (1), A is each independently CN, COCH3 or COOX, B is COOX, X is each independently H, a C1 to 20 substituted or unsubstituted alkyl group and x and y are each independently the number of 0 to 10. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
A simple, efficient and green procedure for Michael addition catalyzed by [C4dabco]OH ionic liquid
Keithellakpam, Sanjoy,Laitonjam, Warjeet S.
, p. 767 - 770 (2014/06/09)
A dabco-based basic ionic liquid, 1-butyl-4-aza-1-azaniabicyclo[2.2.2] octane hydroxide, has been developed as a catalyst for a convenient and rapid method for the Michael addition of active methylene compounds to α,β-unsaturated carboxylic esters and nitriles. The method is very simple, and the yields are very high. The catalyst can be recycled several times without much loss of activity.
A route to a tetrabenzothiazole from Michael bis-addition compounds
Wang, Guowei,Zhuang, Linghua,Wang, Jintang
experimental part, p. 212 - 213 (2009/12/03)
An efficient and practical synthesis of a tetrabenzothiazole has been developed by condensation of Michael bisadducts with 2-aminothiophenol.
Sodium tetramethoxyborate: An efficient catalyst for Michael additions of stabilized carbon nucleophiles
Campana, Araceli G.,Fuentes, Noelia,Gomez-Bengoa, Enrique,Mateo, Cristina,Oltra, J. Enrique,Echavarren, Antonio M.,Cuerva, Juan M.
, p. 8127 - 8130 (2008/02/12)
(Chemical Equation Presented) Sodium tetramethoxyborate, easily prepared by reaction of inexpensive sodium borohydride with methanol, possesses a suitable combination of a Lewis base and a Lewis acid to catalyze Michael reactions at room temperature under
Ionic liquid as catalyst and solvent: the remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds
Ranu, Brindaban C.,Banerjee, Subhash,Jana, Ranjan
, p. 776 - 782 (2007/10/03)
A basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide, [bmIm]OH, catalyzes the Michael addition of active methylene compounds to conjugated ketones, carboxylic esters and nitriles. It further catalyzes the addition of thiols to α,β-acetylenic ketones and alkylation of 1,3-dicarbonyl and -dicyano compounds. The Michael addition to α,β-unsaturated ketones proceeds in the usual way, giving the monoaddition products, whereas addition to α,β-unsaturated esters and nitriles leads exclusively to the bis-addition products. The α,β-acetylenic ketones undergo double conjugate addition with thiols producing β-keto 1,3-dithio-derivatives. In the alkylation reaction the acyclic 1,3-diketones are monoalkylated, whereas cyclic ketones undergo dialkylation under identical conditions. All these reactions were carried out without any organic solvent. The ionic liquid can also be recycled.
Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmIm]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles
Ranu, Brindaban C.,Banerjee, Subhash
, p. 3049 - 3052 (2007/10/03)
(Chemical Equation Presented) A task-specific ionic liquid, [bmIm]OH, has been introduced as a catalyst and as a reaction medium in Michael addition. Very interestingly, although the addition to α,β-unsaturated ketones proceeds in the usual way, giving the monoaddition products, this ionic liquid always drives the reaction of open-chain 1,3-dicarbonyl compounds with α,β-unsaturated esters and nitriles toward bis-addition to produce exclusively bis-adducts in one stroke.
Michael reaction of stabilized carbon nucleophiles catalyzed by [RuH2(PPh3)4]
Gómez-Bengoa, Enrique,Cuerva, Juan M.,Mateo, Cristina,Echavarren, Antonio M.
, p. 8553 - 8565 (2007/10/03)
The Michael reaction of active methylene compounds lacking cyano groups such as malonates, β-ketoesters, 1,3-diketones, 1,1-disulfones, nitrocompounds, Meldrum acid, and anthrone with common acceptors proceeds in acetonitrile solution in the presence of [RuH2(PPh3)4] as the catalyst. Cyano acetates, more acidic than malonates in organic solvents, are also excellent substrates for this reaction. In a number of cases, intramolecular aldol reactions catalyzed by [RuH2(PPh3)4] were also observed as side reactions. Catalysis by other ruthenium and rhodium complexes has been examined. Selectivity studies performed with malonate and disulfone donors indicate that the catalyst selectively activates Michael donors that can coordinate with ruthenium(II). Additionally, it has been shown that the reaction requires the presence of free phosphine. Therefore, the Michael reaction of stabilized enolates appears to be a ruthenium- and phosphine-catalyzed reaction. From a practical point of view, the use of readily prepared [RuH2(PPh3)4] as the catalyst in acetonitrile provided the best solution for the Michael reaction of active methylene compounds.
