On the Reaction of Cyanamides with N-Alkylnitrilium and N,N-Dialkylcyanamidium Salts

N-Alkylnitrilium and NN-dialkylcyanamidium, salts I and 2 undergo ene reactions with cyanamides 4 to afford 2-azoniaallene salts 7 and 9 in which the N-alkylnitrilium salts I react its the ene, and the cynamides 4 react as the enophile components. Competing with the ene reaction, N-alkylnitrilium salts I undergo [2(+)+2+2] cycloaddition to furnish triazinium salts 8. 2-Azoniaallene salts react with alcohols to afford alkoxy amino derivatives 10 and 12, which yield iminium salts 11 and ketals/acetals upon further reaction with alcohols. The Constitution of the 2-azoniaallene 7 and 9 and triazinium salts 8 was secured by elemental analyses and spectral properties (IR and NMR).