Dicationic Electrophiles from Olefinic Amines in Superacid⊥
journal contributionposted on 30.05.2003 by Yun Zhang, Aaron McElrea, Gregorio V. Sanchez, Dat Do, Alma Gomez, Sharon L. Aguirre, Rendy, Douglas A. Klumpp
Any type of content formally published in an academic journal, usually following a peer-review process.
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 CF3SO3H (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.