title: Superelectrophiles and the effects of trifluoromethyl substituents.
abstract: Trifluoromethyl-substituted superelectrophiles were generated in superacid (CF(3)SO(3)H), and their chemistry was examined. The strong electron-withdrawing properties of the trifluoromethyl group are found to enhance the electrophilic character at cationic sites in superelectrophiles. This leads to greater positive-charge delocalization in the superelectrophiles. These effects are manifested by the unusual chemo-, regio-, and stereoselectivities shown by the superelectrophiles in chemical reactions.
authors.affiliation: Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: O'Connor
authors.forename: Kenneth N
authors.initials: KN
authors.lastname: Boblak
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Topinka
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Kindelin
authors.forename: Jason M
authors.initials: JM
authors.lastname: Briski
authors.forename: Chong
authors.initials: C
authors.lastname: Zheng
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Klumpp
mesh_terms: D005463:Fluoroacetates; D008698:Mesylates / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry
chemical_list: D005463:Fluoroacetates; D008698:Mesylates; D011725:Pyridines; D014269:Trifluoroacetic Acid; C012077:trifluoromethanesulfonic acid