Reaction of beta-trifluoromethyl vinamidinium salt with carbon nucleophiles

1,1,5,5-Tetramethyl-3-trifluoromethyl-1,5-diaza-1,3-pentadienium chloride ( beta -trifluoromethyl vinamidinium salt) 1 reacted smoothly with various ty pes of enolates generated from ketones and esters to give the corresponding mono-addition-deamination products, dienaminones 2 and dienaminoates 3, re spectively, in moderate to good yields. The reaction with carbanions from n itromethane, methyl phenyl sulfone, and acetonitrile also produced the corr esponding dienamine derivatives 4, 6 in moderate yields. Interestingly, the carbanion from malononitrile participated well in the reaction with 1 to a fford di-addition-deamination product, diisopropylammonium 1,1,5,5-tetracya no-3-trifluoromethyl-1,3-pentadienide (5) in quantitative yield. (C) 2001 E lsevier Science B.V. All tights reserved.