Lewis- or Brønsted-acid assisted formation of open-chain vinamidinium salts from N,N′-diarylformamidines and acetone

Abstract
An unorthodox reaction of ArNC(H)N(H)Ar (Ar = phenyl, tolyl) with acetone in the presence of a Lewis or Brølnsted acid entails the cleavage of a C–N bond of the formamidine; subsequent incorporation of two carbon atoms of the acetone molecule yields the vinamidinium species N-[3-(phenylamino)-2-propenylidene]benzenaminium tetrafluoroborate 1, or the corresponding p-tolyl analogue 2.

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