Quantum Chemical Insights into the Mechanism of the TADDOL−TiCl2Catalyzed Diels−Alder Reactions

1998 ◽  
Vol 63 (7) ◽  
pp. 2321-2324 ◽  
Author(s):  
J. I. García ◽  
V. Martínez-Merino ◽  
J. A. Mayoral
Keyword(s):  
Quantum Chemical ◽  
Diels Alder

Quantum-chemical investigation of the Diels-Alder reaction in condensed isoindoles with a nodal nitrogen atom

1988 ◽  
Vol 24 (2) ◽  
pp. 179-185
Author(s):  
V. A. Kovtunenko ◽  
Z. V. Voitenko ◽  
L. I. Savranskii ◽  
A. K. Tyltin ◽  
F. S. Babichev
Keyword(s):  
Nitrogen Atom ◽  
Quantum Chemical ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chemical Investigation ◽  
Quantum Chemical Investigation ◽  
Diels Alder Reaction

scholarly journals Why are rhodanines less efficient reagents in Diels–Alder reactions than isorhodanines? A quantum chemical study

2019 ◽  
Vol 25 (7) ◽  
Author(s):  
Waldemar Tejchman ◽  
Michal Michalski ◽  
Krzysztof K. Zborowski ◽  
Slawomir Berski
Keyword(s):  
Quantum Chemical ◽  
Quantum Chemical Study ◽  
Chemical Study ◽  
Diels Alder

On the Solvent and Temperature Driven Stereoselectivity of the Diels-Alder Cycloaddition Reactions of Furan with Maleic Anhydride and Maleimide

2019 ◽  
Author(s):  
Veejendra Yadav ◽  
Dasari L V K Prasad ◽  
Arpita Yadav ◽  
Kedar Yadav
Keyword(s):  
Free Energy ◽  
Maleic Anhydride ◽  
Gas Phase ◽  
Quantum Chemical ◽  
Room Temperature ◽  
Experimental Studies ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Endo Isomer ◽  
Equilibrium Process

In quantum chemical calculations, the Diels-Alder cycloaddition reaction of maleic anhydride with furan favors the endo-isomer kinetically in the gas phase. This preference, however, changes in favor of the exo-isomer on inclusion of solvent effects. For example, in acetonitrile, the exo-isomer was calculated to form twice as fast as the endo-isomer at room temperature, an observation that corroborates well with the experiments. The free energy change of the reaction is such that it allows faster reversal of the endo-isomer to the reactants in an equilibrium process and, thus, the predominance of the more stable exo-isomer eventually. The reaction of maleimide with furan is similar to that of maleic anhydride. However, it favors predominantly endo selectivity at temperatures below 320 K which is in excellent agreement with the experimental studies of temperature dependence of this DA reaction. Further, a gedanken calculation of the DA reaction of cyclopropene with furan has been investigated to delineate the effect of the retro-pathway on the stereoselectivity.

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