The 3-trifluoromethylsulfonyloxy-1-hexeniminium triflate 1 reacts with two equivalents of an aliphatic nitrile or of benzonitrile to give the 4-(2-diethylaminovinyl)pyrimidinediium bis(triflates) 4, which can be deprotonated to give the monoprotonated or neutral pyrimidines 5 and 6, respectively. When the related 1-phenyl-substituted iminium salt 7 is heated in acetonitrile at 140°, 1,5-cyclization of the cation leading to indane derivative 8 competes with formation of the pyrimidinium salt 9. X-ray crystal structure determination reveals significant differences in the bond lengths of mono-and diprotonated 4-(2-diethylaminovinyl)pyrimidines 5a and 4a.
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