title: Use of chiral ionic liquids as solvents for the enantioselective photoisomerization of dibenzobicyclo[2.2.2]octatrienes.
abstract: [Reaction: see text] Six chiral ionic liquids were prepared and evaluated as "chiral induction solvents" in which two different dibenzobicyclo[2.2.2]octatrienes were photoisomerized to chiral products. Enantiomeric excesses from 3 to 12% were obtained from the photochemical di-pi-methane rearrangement. Results indicate that the chiral induction derives from an ion pairing interaction of the deprotonated diacids with the ionic liquid cation. This is the first report on chiral induction via a chiral IL for an irreversible, unimolecular photochemical isomerization.
authors.affiliation: Chemistry Department, Iowa State University, Ames, Iowa 50011, USA.
authors.forename: Jie
authors.initials: J
authors.lastname: Ding
authors.forename: Vasumathi
authors.initials: V
authors.lastname: Desikan
authors.forename: Xinxin
authors.initials: X
authors.lastname: Han
authors.forename: Tom L
authors.initials: TL
authors.lastname: Xiao
authors.forename: Rongfang
authors.initials: R
authors.lastname: Ding
authors.forename: William S
authors.initials: WS
authors.lastname: Jenks
authors.forename: Daniel W
authors.initials: DW
authors.lastname: Armstrong
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D003500:Cyclization; D007477:Ions; D015394:Molecular Structure; D010777:Photochemistry; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001555:Benzene Derivatives; D007477:Ions; D011084:Polycyclic Aromatic Hydrocarbons; D012997:Solvents