High-pressure effects on the Diels–Alder reaction in room temperature ionic liquids

2007 ◽  
Vol 20 (2) ◽  
pp. 109-114 ◽  
Author(s):  
Ana Vidiš ◽  
Gábor Laurenczy ◽  
Ernst Küsters ◽  
Gottfried Sedelmeier ◽  
Paul J. Dyson
Keyword(s):  
High Pressure ◽  
Ionic Liquids ◽  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Pressure Effects ◽  
Room Temperature Ionic Liquids ◽  
Diels Alder Reaction ◽  
High Pressure Effects

scholarly journals Solvation Effects Drive the Selectivity in Diels-Alder Reaction Under Hyperbaric Conditions

2020 ◽  
Author(s):  
Daniele Loco ◽  
Riccardo Spezia ◽  
François Cartier ◽  
Isabelle Chataigner ◽  
Jean-Philip Piquemal
Keyword(s):  
High Pressure ◽  
Alder Reaction ◽  
Diels Alder ◽  
Pressure Effects ◽  
Reaction Products ◽  
Diels Alder Reaction ◽  
Kinetics Of ◽  
High Pressure Effects ◽  
Reaction Profile ◽  
Hyperbaric Conditions

High pressure effects on the Diels-Alder reaction in condensed phase are investigated by means oftheoretical methods, employing advanced multiscale modeling approaches based on physically groundedmodels. The simulations reveal how the increase of pressure from 1 to 10000 atm does not affect thestability of the reaction products, modifying the kinetics of the process by lowering considerably thetransition state energy. The reaction profile at high pressure remarkably differs from that at 1 atm,showing a submerged TS and a pre–TS structure lower in energy. The different solvation between endoand exo pre–TS is revealed as the driving force pushing the reaction toward a much higher preferencefor the endo product at high pressure.

scholarly journals Solvation effects drive the selectivity in Diels–Alder reaction under hyperbaric conditions

2020 ◽  
Vol 56 (49) ◽  
pp. 6632-6635
Author(s):  
Daniele Loco ◽  
Riccardo Spezia ◽  
François Cartier ◽  
Isabelle Chataigner ◽  
Jean-Philip Piquemal
Keyword(s):  
High Pressure ◽  
Multiscale Modeling ◽  
Condensed Phase ◽  
Alder Reaction ◽  
Diels Alder ◽  
Pressure Effects ◽  
Theoretical Methods ◽  
Diels Alder Reaction ◽  
High Pressure Effects ◽  
Hyperbaric Conditions

High pressure effects on the Diels–Alder reaction in condensed phase are investigated by means of theoretical methods, employing advanced multiscale modeling approaches based on physically grounded models.

scholarly journals Solvation Effects Drive the Selectivity in Diels-Alder Reaction Under Hyperbaric Conditions

2020 ◽  
Author(s):  
Daniele Loco ◽  
Riccardo Spezia ◽  
François Cartier ◽  
Isabelle Chataigner ◽  
Jean-Philip Piquemal
Keyword(s):  
High Pressure ◽  
Alder Reaction ◽  
Diels Alder ◽  
Pressure Effects ◽  
Reaction Products ◽  
Diels Alder Reaction ◽  
Kinetics Of ◽  
High Pressure Effects ◽  
Reaction Profile ◽  
Hyperbaric Conditions

High pressure effects on the Diels-Alder reaction in condensed phase are investigated by means oftheoretical methods, employing advanced multiscale modeling approaches based on physically groundedmodels. The simulations reveal how the increase of pressure from 1 to 10000 atm does not affect thestability of the reaction products, modifying the kinetics of the process by lowering considerably thetransition state energy. The reaction profile at high pressure remarkably differs from that at 1 atm,showing a submerged TS and a pre–TS structure lower in energy. The different solvation between endoand exo pre–TS is revealed as the driving force pushing the reaction toward a much higher preferencefor the endo product at high pressure.

Rationalisation of Solvent Effects in the DielsAlder Reaction Between Cyclopentadiene and Methyl Acrylate in Room Temperature Ionic Liquids

2005 ◽  
Vol 347 (2-3) ◽  
pp. 266-274 ◽  
Author(s):  
Ana Vidiš ◽  
C. André Ohlin ◽  
Gábor Laurenczy ◽  
Ernst Küsters ◽  
Gottfried Sedelmeier ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Solvent Effects ◽  
Methyl Acrylate ◽  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Room Temperature Ionic Liquids ◽  
Diels Alder Reaction

scholarly journals Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

2015 ◽  
Vol 11 ◽  
pp. 576-582 ◽  
Author(s):  
Grzegorz Mlostoń ◽  
Paulina Grzelak ◽  
Maciej Mikina ◽  
Anthony Linden ◽  
Heinz Heimgartner
Keyword(s):  
High Pressure ◽  
Room Temperature ◽  
Thermal Conditions ◽  
Alder Reaction ◽  
Diels Alder ◽  
Hydrogen Shift ◽  
Diels Alder Reaction ◽  
Shift Sequence

Selected hetaryl and aryl thioketones react with acetylenecarboxylates under thermal conditions in the presence of LiClO4 or, alternatively, under high-pressure conditions (5 kbar) at room temperature yielding thiopyran derivatives. The hetero-Diels–Alder reaction occurs in a chemo- and regioselective manner. The initially formed [4 + 2] cycloadducts rearrange via a 1,3-hydrogen shift sequence to give the final products. The latter were smoothly oxidized by treatment with mCPBA to the corresponding sulfones.

scholarly journals Ionic liquid promoted Diels-Alder Reaction between anthrone and maleimides

2010 ◽  
Vol 8 (2) ◽  
pp. 356-360 ◽  
Author(s):  
Nitin Mirgane ◽  
Sandip Kotwal ◽  
Anil Karnik
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Room Temperature ◽  
Alder Reaction ◽  
Dual Role ◽  
Diels Alder ◽  
Environmentally Benign ◽  
Green Solvents ◽  
Imidazolium Ionic Liquid ◽  
Diels Alder Reaction

AbstractIonic liquids (IL) are gaining importance as green solvents. Imidazolium ionic liquid [bmim]+[Cl]−, an environmentally benign solvent, was found to promote the Diels-Alder reaction between anthrone and maleimides at room temperature with excellent yields. The ionic liquid played a dual role as solvent and catalyst.

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