Dicationic electrophiles from olefinic amines in superacid.

@article{Zhang2003DicationicEF,
  title={Dicationic electrophiles from olefinic amines in superacid.},
  author={Yun Zhang and Aaron McElrea and Gregorio S{\'a}nchez and Dat Tien Do and Alma Gomez and Sharon L. Aguirre and Rendy Rendy and Douglas A. Klumpp},
  journal={The Journal of organic chemistry},
  year={2003},
  volume={68 13},
  pages={
          5119-22
        }
}
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… 

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References

Dicationic electrophiles from olefinic amines in superacid.

  • 2003