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  4. Rationalisation of solvent effects in the diels-alder reaction between cyclopentadiene and methyl acrylate in room temperature ionic liquids
 
research article

Rationalisation of solvent effects in the diels-alder reaction between cyclopentadiene and methyl acrylate in room temperature ionic liquids

Vidis, A  
•
Ohlin, CA
•
Laurenczy, G  
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2005
ADVANCED SYNTHESIS & CATALYSIS

The Diels-Alder reaction between cyclopentadiene and methyl acrylate in ionic liquids has been studied in detail. The effect of contamination of the ionic liquids by common impurities, viz. sodium and chloride ions, and water, on the selectivity has been investigated. The presence of high concentrations of chloride was found to decrease the selectivity. Anion and, in particular, cation effects have been investigated using an extensive series of air-stable room temperature ionic liquids, and kinetic parameters have been determined. It has been found that strongly interacting groups, particularly electrophilic moieties on the cation, accelerate the formation of the endo products. Substrate solubility intimately connected to the selectivity was found to be mainly anion dependent. An NMR-based solvent parameter scale and semi-empirical models are used to analyse the results and provide a tool for the prediction of selectivities in ionic liquids.

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Type
research article
DOI
10.1002/adsc.200404301
Web of Science ID

WOS:000227414500010

Author(s)
Vidis, A  
Ohlin, CA
Laurenczy, G  
Kusters, E
Sedelmeier, G
Dyson, PJ  
Date Issued

2005

Published in
ADVANCED SYNTHESIS & CATALYSIS
Volume

347

Issue

2-3

Start page

266

End page

274

Subjects

solvatochromic comparison method

•

solvation energy relationships

•

hydrophobic interactions

•

carbon-monoxide

•

molten-salts

•

pi-star

•

water

•

selectivity

•

polarity

•

alpha

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCOM  
Available on Infoscience
November 9, 2005
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/219923
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