Maleic Anhydride And Furan Reaction

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Abstruse

In quantum chemical calculations, the Diels–Alder (DA) cycloaddition reaction of furan with maleic anhydride 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 grade 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 procedure and, thus, the predominance of the more than stable exo‐isomer somewhen. The reaction of furan with maleimide is similar to that with maleic anhydride. However, it predominantly favors endo‐selectivity at temperatures beneath 320 One thousand, which is also in excellent agreement with the experimental studies of temperature dependence of this DA reaction. Further, a gedanken calculation of the DA reaction of furan with cyclopropene has been investigated to delineate the result of the retro‐pathway on stereoselectivity.

The kinetic preference of the Diels–Alder reaction of maleic anhydride with furan changes from endo in the gas phase to exo on inclusion of solvent effects. The complimentary free energy change of the reaction is such that information technology allows faster reversal of the endo‐isomer to the reactants in an equilibrium process to ensure predominance of the more stable exo‐isomer. The reaction of maleimide with furan, yet, favors endo‐isomer at temperatures below 320 Yard in fantabulous agreement with the experiments.

Keywords

Diels–Alder reaction

furan

kinetic control

maleic anhydride

maleimide

solvent‐ and temperature‐driven stereoselectivity

thermodynamic control

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