Dicationic electrophiles from olefinic amines in superacid.
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.
Zhang
Yun
Y
Department of Chemistry, California State Polytechnic University, 3801 West Temple Avenue, Pomona, California 91768, USA.
McElrea
Aaron
A
Sanchez
Gregorio V
GV
Do
Dat
D
Gomez
Alma
A
Aguirre
Sharon L
SL
Rendy
Rendy
R
Klumpp
Douglas A
DA