Solvate Ionic Liquids as Reaction Media for Electrocyclic Transformations

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.

Solvate ionic liquids have been explored for their suitability as reaction media for organic transformations. These ILs are able to undergo typical optimisation procedures, are inexpensive, and easy to handle.

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