Solvate Ionic Liquids as Reaction Media for Electrocyclic Transformations. Issue 5 (25th January 2016)

• Record Type: Journal Article
• Authors: Eyckens, Daniel J.; Champion, Megan E.; Fox, Bronwyn L.; Yoganantharajah, Prusothman; Gibert, Yann; Welton, Tom; Henderson, Luke C.
• Is Part Of: European journal of organic chemistry. Issue 5(2016)
• Page Start: 913
• Page End: 917
• Publication Date: 2016-01-25
• Subjects: Ionic liquids -- Lithium -- Solvates -- Lewis acids -- Acceptor number; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501614
• Languages: English
• ISSNs: 1434-193X

Abstract

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 5M lithium perchlorate in diethyl ether. The Gutmann acceptor number ( AN ) of these solvate ionic liquids has also been determined by 31 P NMR spectroscopy to be 26.5, thus being modest Lewis acids. Abstract : 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.