Organic Chemistry Portal



Dicationic Electrophiles from Olefinic Amines in Superacid

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

*Department of Chemistry and Biochemistry, The Michael Faraday Laboratories, NIU, DeKalb, IL 60115-2862, Email:

Y. Zhang, A. McElrea, G. V. Sanchez, Jr., D. Do, A. Gomez, S. L . Aguirre, R. Rendy, D. A. Klumpp, J. Org. Chem., 2003, 68, 5119-5122.

DOI: 10.1021/jo030024z (free Supporting Information)


A superacid-catalyzed reaction of various olefinic amines and related compounds with benzene gives addition products in good yields. The formation of reactive, dicationic electrophiles is proposed.

see article for more examples

formation of dicationic species

Key Words

Friedel-Crafts Alkylation, electrophilic aromatic substitution, diarylmethanes, alkylation of arenes

ID: J42-Y2003-160