PYRROLES, IMIDAZOLES AND POLY(VINAMIDINES) FROM BIS(VINAMIDINIUM SALTS)

The reaction of bis(vinamidinium salts) (5a, 6) and amidinium-vinamidi nium salts (7, 21) with primary amines was studied. Whereas the conden sation of 6 and 7a with p-phenylenediamine and 4,4'diaminostilbene gav e rise to poly meric vinamidines (12, 18), 5a and 7b reacted with arom atic amines and diamines to give pyrrole and imidazole derivatives. Th e reaction of p-aminophenylacetic acid with DMF-POCl3 produced a new a midinium-vinamidinium salt (21) which could be converted into a donor- acceptor substi-tuted diazaterphenyl derivative (22) displaying a stro ng solvatochromism. - The crystal structure analysis of the 2,2'-bis(v inamidinium salt) 5b revealed a 73 degrees twist angle between the pla nes of the vinamidinium moieties.