A [2 + 2] cycloaddition route to dimethylaminomethylene vinamidinium salts

  • Davies I
  • Tellers D
  • Shultz C
 et al. 
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[reaction: see text] Trifluoropropanoic acid reacts with 1 equiv of POCl3 in DMF to generate the trifluoromethyl enamine (7). At this stage, two reaction manifolds are available. The expected reaction with additional POCl3 generates the 2-trifluoromethyl vinamidinium salt (3c). However, thermally driven loss of fluoride generates an iminium ion, which sets the stage for a [2 + 2] cycloaddition to ultimately generate the dimethylaminomethylene vinamidinium salt (1).

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  • Ian W. Davies

  • David M. Tellers

  • C. Scott Shultz

  • Fred J. Fleitz

  • Dongwei Cai

  • Yongkui Sun

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