Internal and external factors promoting the Diels-Alder reaction

Simple Cope and Claisen rearrangements were investigated in an ionic liquid and a range of molecular solvents through a series of kinetic studies. Analysis of the solvent effects on the Cope rearrangement of 3‐phenyl‐1,5‐hexadiene indicated that a solvophobic effect was responsible for the observed rate enhancement in the ionic liquid, and that this was due to preferential solvation of the transition state. A similar solvophobic effect contributes to the ionic liquid solvent effect on the Claisen rearrangement of allyl vinyl ether, although the ability of the ionic liquid to stabilise the incipient charges in the transition state also likely contributes to the rate increase observed in the ionic liquid solvent. The activation parameter data suggest that in this case the ionic liquid was interacting with species along the reaction coordinate through general coulombic interactions (more acetonitrile‐like) rather than through hydrogen‐bonding interactions (less ethanol‐like).

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Kinetic and equilibrium parameters of [4+2] cycloaddition reaction of 2,6-dimethylnaphthalene with 4-phenyl-1,2,4-triazoline-3,5-dione

Kiselev

Kashaeva

Potapova

et al. 2014

Russ Chem Bull

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Internal and external factors promoting the Diels-Alder reaction

Cited by 6 publications

References 97 publications

ChemInform Abstract: Internal and External Factors Promoting the Diels—Alder Reaction

ChemInform Abstract: Internal and External Factors Promoting the Diels—Alder Reaction

Investigating Solvent Effects of an Ionic Liquid on Pericyclic Reactions through Kinetic Analyses of Simple Rearrangements

Kinetic and equilibrium parameters of [4+2] cycloaddition reaction of 2,6-dimethylnaphthalene with 4-phenyl-1,2,4-triazoline-3,5-dione

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