Reactive dications: the superacid-catalyzed reactions of alkynes bearing adjacent N-heterocycles or amine groups

J Org Chem. 2004 Nov 12;69(23):8108-10. doi: 10.1021/jo040218u.

Abstract

A variety of aminoalkynes and related heterocycles are reacted in the Bronsted superacid CF(3)SO(3)H (triflic acid), and products are obtained in generally good yields (69-99%) from Friedel-Crafts-type reactions. The reactions are consistent with the formation of novel dicationic intermediates having a vinyl cationic site and an adjacent protonated N-heterocycle or ammonium cation.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkynes / chemistry*
  • Amines / chemistry*
  • Catalysis
  • Cations / chemistry
  • Heterocyclic Compounds / chemistry*
  • Indicators and Reagents
  • Molecular Structure
  • Quaternary Ammonium Compounds / chemistry

Substances

  • Alkynes
  • Amines
  • Cations
  • Heterocyclic Compounds
  • Indicators and Reagents
  • Quaternary Ammonium Compounds