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.

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.

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 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.

Simple, efficient total synthesis of cantharidin via a high-pressure Diels-Alder reaction

1980 ◽  
Vol 102 (22) ◽  
pp. 6893-6894 ◽  
Author(s):  
William G. Dauben ◽  
Carl R. Kessel ◽  
Kazuo H. Takemura
Keyword(s):  
High Pressure ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

ChemInform Abstract: The High Pressure-Mediated Intramolecular Diels-Alder Reaction of Furans: Factors Controlling Cycloaddition with Monoactivated Dienophiles.

ChemInform ◽  
1989 ◽  
Vol 20 (14) ◽  
Author(s):  
L. M. HARWOOD ◽  
S. A. LEEMING ◽  
N. S. ISAACS ◽  
G. JONES ◽  
J. PICKARD ◽  
...  
Keyword(s):  
High Pressure ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

High Pressure Diels-Alder Reaction of 1-Methyl-2(1H)-pyridones Having a Phenyl Group with N-Phenylmaleimide

Heterocycles ◽  
1990 ◽  
Vol 30 (1) ◽  
pp. 359 ◽  
Author(s):  
Hiroshi Tomisawa ◽  
Hiroto Nakano ◽  
Hiroshi Hongo
Keyword(s):  
High Pressure ◽  
Phenyl Group ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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