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Solvate Ionic Liquids as Reaction Media for Electrocyclic Transformations
Author(s) -
Eyckens Daniel J.,
Champion Megan E.,
Fox Bronwyn L.,
Yoganantharajah Prusothman,
Gibert Yann,
Welton Tom,
Henderson Luke C.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501614
Subject(s) - ionic liquid , chemistry , cycloaddition , lithium perchlorate , imide , solvent , lithium (medication) , ionic bonding , lewis acids and bases , perchlorate , organic chemistry , diethyl ether , polymer chemistry , ion , catalysis , electrolyte , medicine , electrode , endocrinology
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 31 P NMR spectroscopy to be 26.5, thus being modest Lewis acids.