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A [2 + 2] cycloaddition route to dimethylaminomethylene vinamidinium salts
Ian W Davies1, David M Tellers, C Scott Shultz
1Department of Process Research and the Reaction Engineering Laboratory of Chemical Engineering R&D, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065-0900, USA. ian_davies1@merck.com
Organic Letters
|August 17, 2002
Abstract:
[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).