112296-87-4Relevant academic research and scientific papers
Intramolecular diels-alder reaction in ionic liquids: Effect of ion-specific solvent friction
Tiwari, Shraeddha,Khupse, Nageshwar,Kumar, Anil
supporting information; experimental part, p. 9075 - 9083 (2009/04/06)
(Chemical Equation Presented) The present work aims at understanding the role of viscosity or solvent friction in ionic liquids for an intramolecular Diels-Alder (IMDA) reaction of (E)-1-phenyl-4-[2-(3-methyl-2-butenyloxy) benzylidene]-5-pyrazolone (1). The results have been analyzed on the basis of the current theoretical models, and their failure to account for the observed trends is discussed in terms of "effective" viscosity or microviscosity. The rates of the reaction decrease with the increasing viscosity of the ionic liquids. As evident from the anionic effect, the solute-solvent specific interactions play a role in governing the kinetics of the reaction. The lower viscosities of the bistrifluoromethanesulfonimide [NTf2] - based ionic liquids as compared to those based on tetrafluoroborate [BF4]- anion fail to result in a corresponding acceleration in the rates of the reaction. These contradictory results indicate that solvent microviscosity, rather than the bulk macroscopic viscosity, should be the criteria for selecting the ionic liquids as reaction media.
SOLVENT EFFECT AS THE RESULT OF FRONTIER MOLECULAR ORBITAL INTERACTION. IV. A PARALLEL BETWEEN SOLVENT EFFECT AND ACID CATALYSIS IN THE INTRAMOLECULAR HETERO-DIELS-ALDER REACTION.
Coda, Andreina Corsico,Desimoni, Giovanni,Faita, Giuseppe,Righetti, Pierpaolo,Tacconi, Gianfranco
, p. 775 - 788 (2007/10/02)
The solvent effect of the intramolecular hetero-Diels-Alder (I.H.D.A.) reaction of 1-phenyl-4--5-pyrazolone (3) was measured in several solvents.The rate increased with increases in the Acceptor Number of the solvent,
