Superelectrophiles and the effects of trifluoromethyl substituents.
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.
O'Connor
Matthew J
MJ
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA.
Boblak
Kenneth N
KN
Topinka
Michael J
MJ
Kindelin
Patrick J
PJ
Briski
Jason M
JM
Zheng
Chong
C
Klumpp
Douglas A
DA
D005463:Fluoroacetates; D008698:Mesylates / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry
D005463:Fluoroacetates; D008698:Mesylates; D011725:Pyridines; D014269:Trifluoroacetic Acid; C012077:trifluoromethanesulfonic acid