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. 2003 Jun 27;68(13):5119-22.
doi: 10.1021/jo030024z.

Dicationic electrophiles from olefinic amines in superacid

Yun Zhang  1 , Aaron McElrea, Gregorio V Sanchez Jr, Dat Do, Alma Gomez, Sharon L Aguirre, Rendy Rendy, Douglas A Klumpp
Affiliations

Dicationic electrophiles from olefinic amines in superacid

Yun Zhang et al. J Org Chem. .

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.

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