Solvate ionic liquids as reaction media for electrocyclic transformations

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Title: Solvate ionic liquids as reaction media for electrocyclic transformations
Authors: Eyckens, DJ
Champion, ME
Fox, BL
Yoganantharajah, P
Gibert, Y
Welton, T
Henderson, LC
Item Type: Journal Article
Abstract: Solvate ionic liquids (SILs) consisting of lithium bis(trifluoromethylsulfonyl)imide dissolved in tri- or tetraglyme have recently emerged as a novel class of ionic liquids. Herein, the first use of solvate ionic liquids as a replacement for molecular solvents in electrocyclization reactions is reported. The SILs promoted both Diels–Alder and [2+2] cycloaddition reactions, compared to an appropriate molecular solvent, and 5 m lithium perchlorate in diethyl ether. The Gutmann acceptor number (AN) of these solvate ionic liquids has also been determined by 31P NMR spectroscopy to be 26.5, thus being modest Lewis acids.
Issue Date: 25-Jan-2016
Date of Acceptance: 28-Dec-2015
URI: http://hdl.handle.net/10044/1/30825
DOI: https://dx.doi.org/10.1002/ejoc.201501614
ISSN: 1434-193X
Publisher: Wiley-VCH Verlag
Start Page: 913
End Page: 917
Journal / Book Title: European Journal of Organic Chemistry
Volume: 2016
Issue: 5
Copyright Statement: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article, which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201501614/abstract
Keywords: Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
Ionic liquids
Lithium
Solvates
Lewis acids
Acceptor number
PERCHLORATE-DIETHYL-ETHER
DIELS-ALDER REACTIONS
LITHIUM PERCHLORATE
LEWIS ACIDITY
CATALYSIS
TEMPERATURE
STABILITY
MIXTURES
SOLVENTS
Organic Chemistry
0305 Organic Chemistry
0304 Medicinal And Biomolecular Chemistry
Publication Status: Published
Appears in Collections:Chemistry
Catalysis and Advanced Materials
Faculty of Natural Sciences



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