title: Dicationic electrophiles from olefinic amines in superacid.
abstract: This paper describes the superacid-catalyzed chemistry of olefinic amines and related compounds. A variety of olefinic amines are found to react with benzene in CF(3)SO(3)H (triflic acid) to give addition products in good yields (75-99%), including the pharmaceutical agents fenpiprane and prozapine. A general mechanism is proposed that invokes the formation of reactive, dicationic electrophiles and the direct observation of a diprotonated species is reported from low-temperature NMR experiments. This chemistry is also used to conveniently prepare functionalized polystyrene beads having pendant amine groups.
authors.affiliation: Department of Chemistry, California State Polytechnic University, 3801 West Temple Avenue, Pomona, California 91768, USA.
authors.forename: Yun
authors.initials: Y
authors.lastname: Zhang
authors.forename: Aaron
authors.initials: A
authors.lastname: McElrea
authors.forename: Gregorio V
authors.initials: GV
authors.lastname: Sanchez
authors.forename: Dat
authors.initials: D
authors.lastname: Do
authors.forename: Alma
authors.initials: A
authors.lastname: Gomez
authors.forename: Sharon L
authors.initials: SL
authors.lastname: Aguirre
authors.forename: Rendy
authors.initials: R
authors.lastname: Rendy
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Klumpp