Study of reactions of pyrylium salts with nucleophiles primary amines

During the present investigation, seven variously substituted pyrylium perchlorates were prepared. They were converted into several pyridium perchlorates by reaction with some aliphatic and aromatic amines. The IR, UV and NMR spectra of the latter compounds have shown some characteristic features, which were discussed in some details, especially useful were the NMR spectra of the N-ally pyridnium perchlorates, which made it possible to predict the probable conformation of the ally group with respect to the pyridinium ring. The relationship between the structure and the reduced reactivity was demonstrated chemically by the slow reaction with bromine or with potassium permanganate. 11 tabs.; 26 figs.; 87 refs