17791-32-1Relevant articles and documents
Tandem Diels-Alder aromatization reactions of furans under unconventional reaction conditions - Experimental and theoretical studies
Fraile, Jose M.,Garcia, Jose I.,Gomez, Maria A.,De La Hoz, Antonio,Mayoral, Jose A.,Moreno, Andres,Prieto, Pilar,Salvatella, Luis,Vazquez, Ester
, p. 2891 - 2899 (2001)
Silica-supported Lewis acids are good catalysts for Diels-Alder reactions between furan and acrylonitrile and methyl acrylate at room temperature. When 2,5-dimethylfuran is used as the diene, yields of the Diels-Alder adducts with methyl acrylate are lower, due in part to the appearance of aromatization products. The use of microwave activation results in some cases in good yields of aromatic products and, as such, constitutes a good synthetic route to polysubstituted aromatic compounds. Computational studies on the reaction mechanism and the role of the catalyst on the product distribution show that "hard" Lewis acids, such as aluminum derivatives, make ring-opening of the adduct much easier, affording aromatic products. The theoretical results are in excellent agreement with the relative reactivity observed for the different dienes and dienophiles.
EFFECT OF PRESSURE ON THE DIELS-ALDER REACTION BETWEEN FURAN AND METHYL ACRYLATE
Zhulin, V. M.,Kabotyanskaya, E. B.,Kel'tseva, M. V.,Bogdanov, V. S.,Koreshkov, Yu. D.
, p. 2404 - 2407 (1990)
A study was carried out on the effect of pressure up to 1400 MPa on the Diels-Alder reaction between furan and methyl acrylate at 20 deg C.At atmospheric pressure, the reaction proceeds with 20percent yield after two months, while it proceeds at 1400 MPa with 70percent yield after 2.5 h.The observed volumetric activation effect (-ΔVp(excit.)) of this reaction decreases relatively slightly with increasing pressure and its value at 0.1 MPa (20 cm3/mole) is markedly less than the change in volume upon reaction (-ΔV0 = 29 cm3/mole).The ratio of the endo and exo isomers formed is 2.6 and is independent of the pressure.
Oscillations of reactivity in the [2+4]-cycloaddition of methyl acrylate to furan
Zhulin,Koreshkov, Yu D.,Bogdanov,Kel'Lseva, At V.
, p. 2321 - 2326 (1996)
The kinetics of [2+4|-cycIoaddition of methyl acrylate to furan (Diels-Alder reaction) were studied at 70 °C and 907 MPa, i.e., under conditions where the solvent (benzene) exists in the solid state. It was found that the reactivity exhibits oscillations with astronomic time and that its averaging leads to reaction rate constants, which are close to those expected from the calculations, carried out using the known reaction and activation volume effects and the reactivity at a pressure close to the atmospheric pressure.
High Pressure Organic Chemistry. V. Diels-Alder Reactions of Furan with Acrylic and Maleic Esters
Kotsuki, Hiyoshizo,Nishizawa, Hitoshi,Ochi, Masamitsu,Matsuoka, Kiyoshi
, p. 496 - 499 (1982)
A series of Diels-Alder reactions of furan with acrylic and maleic esters has been investigated under conditions of high pressure.The approximate endo/exo ratios of the adducts with acrylic and maleic esters were 6 : 4 and 8 : 2 respectively.The observed
Regiodivergent addition of phenols to allylic oxides: Control of 1,2- and 1,4-additions for cyclitol synthesis
Moschitto, Matthew J.,Vaccarello, David N.,Lewis, Chad A.
supporting information, p. 2142 - 2145 (2015/02/19)
Control of 1,2- and 1,4-addition of substituted phenols to allylic oxides is achieved by intercepting palladium π-allyl complexes. The interconversion of palladium complexes results in the total synthesis of MK7607, cyathiformine B type, streptol, and a new cyclitol.
Norbornenes in inverse electron-demand diels-alder reactions
Vrabel, Milan,Koelle, Patrick,Brunner, Korbinian M.,Gattner, Michael J.,Lopez-Carrillo, Veronica,De Vivie-Riedle, Regina,Carell, Thomas
supporting information, p. 13309 - 13312 (2013/10/08)
Significant differences in the reactivity of norbornene derivatives in the inverse electron-demand Diels-Alder reaction with tetrazines were revealed by kinetic studies. Substantial rate enhancement for the exo norbornene isomers was observed (see scheme). Quantum-chemical calculations were used to rationalize and support the observed experimental data. Copyright
