Reactions of pyrylium salts with nucleophiles—V

摘要: Abstract N-Aryl-2,4,6-trimethylpyrydinium salts were prepared from 2,4,6-trimethylpyrylium perchlorate and ArNH 2 , the aryl group being p -chloro-, bromo, iodo, methyl-, hydroxy- or amino-phenyl. The reaction of with primary aliphatic amines (methyl, ethyl n-propyl, n-butyl, isopentyl, benzyl, cyclohexyl, n-heptyl n-octadecyl) was found to afford along N-alkylpyridinium salts, N-alkyl-3,5-xylidines. Such cyclizations an aniline derivative known only in reactions pyrylium secondary amines. A third kind product is formed very small yield aromatic amines, larger higher as t-butyl amine; it possibly imino-enol. IR NMR spectra are discussed assignments bands made on basis deuteration amino methyl groups. In N-aryl-2,4,6-trimethylpyridinium upfield shift α-methyl signal implies non-coplanarity pyridinium phenyl rings.