138752-04-2Relevant academic research and scientific papers
High viscosity of ionic liquids causes rate retardation of Diels-Alder reactions
Kumar, Anil,Pawar, Sanjay S.
, p. 1633 - 1637 (2012)
Second order rate constants, k2 have been determined for three bi-molecular Diels-Alder reactions to demonstrate that the high viscosity of ionic liquids can be a detrimental property in carrying out Diels-Alder reactions, if ionic liquids are employed as solvent media. It is possible to enhance the reaction rates of the reaction if a co-solvent is mixed in pure ionic liquid used as a solvent. Science China Press and Springer-Verlag Berlin Heidelberg 2012.
Asymmetrical [4+2]-cycloaddition of (-)-menthyl acrylate and (-)-menthyl methacrylate to cyclopentadiene in the presence of BBr3
Mamedov
, p. 217 - 222 (2007/10/03)
An asymmetrical synthesis of bicyclo[2.2.1]hept-2-enes is described performed by [4+2]-cycloaddition of (-)-menthyl acrylate and (-)-menthyl methacrylate to cyclopentadiene in the presence of BBr3. The effect of different factors on isomer composition, yield, and enantiomeric purity of the compounds obtained was investigated. Kovatch indices were determined and boiling points were estimated with the use of gas-liquid chromatography.
Silica and alumina modified by Lewis acids as catalysts in Diels-Alder reactions of chiral acrylates
Cativiela,Figueras,Garcia,Mayoral,Pires,Royo
, p. 621 - 624 (2007/10/02)
Silica and alumina, modified by treatment with AlClEt2 and TiCl4, are tested as catalysts in the reactions of cyclopentadiene (1) with (-)-methyl acrylate (2a), (R)-O-acryloyl pantolactone (2b) and (S)-O-acryloyl lactate (2c). Silica-modified systems are the most efficient heterogeneous catalysts described to date for this kind of reaction, leading to selectivities similar to those obtained with aluminium homogeneous catalysts. Whereas silica· AlClEt2 is better for the reaction of 2a and 2c, silica· TiCl4 is more suitable for the reaction of 2b.
Effect of clay calcination on clay-catalysed Diels-Alder reactions of cyclopentadiene with methyl and (-)-menthyl acrylates
Cativiela, Carlos,Fraile, Jose M.,Garcia, Jose I.,Mayoral, Jose A.,Pires, Elisabeth,Figueras, Francois,De Menorval, Louis C.
, p. 6467 - 6476 (2007/10/02)
Zn(II) and Fe(III)-exchanged K 10-montmorillonites, activated by several methods, are used as catalysts in the reaction between methyl acrylate and cyclopentadiene. Calcined clays are better catalysts than dried clays. Zn(II) clays, dried and calcined, are compared as catalysts of the asymmetric Diels-Alder reaction between (-)-methyl acrylate and cyclopentadiene. Calcined clay again shows a higher catalytic activity and leads to better percentages of diastereomeric excess. Furthermore, calcined clays are easily recovered with no loss of catalytic properties.
The reaction of optically active menthyl acrylate with cyclopentadiene on γ-alumina
Hondrogiannis,Pagni,Kabalka,Kurt,Cox
, p. 2303 - 2306 (2007/10/02)
The Diels-Alder reaction of optically active menthyl acrylate with cyclopentadiene is catalyzed by γ-alumina. The reaction is very selective, yielding large endo to exo ratios of products and diastereomeric excesses for the endo adduct.
Clay-catalysed asymmetric Diels-Alder reaction of cyclopentadiene with (-)-menthyl acrylate
Cativiela,Figueras,Fraile,Garcia,Mayorall
, p. 953 - 956 (2007/10/02)
Zn(II)-exchanged K10 montmorillonite is shown to be an efficient catalyst for the reaction between cyclopentadiene and (-)-menthyl acrylate, leading to the 1R,2R-cycloadduct with good chemical yield, high % d.e. and excellent endo/exo selectivity.
