Collect. Czech. Chem. Commun. 1983, 48, 511-516

Oxidative elimination of tert-butyl group from α position of quarternary pyridinium salts

Petr Nesvadba and Josef Kuthan

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


Ferricyanide oxidation of 1-methyl-2-tert-butyl-4,6-diphenylpyridinium tetrafluoroborate (I) and its 2,6-ditert-butyl analogue (II) is accompanied by elimination of the 2-substituent with formation of the corresponding 2-pyridones VII and VIII, respectively. On the contrary, oxidation of quarternary salt III with tert-butyl group at 4 position gives a complex reaction mixture from which a small amount of pyrrole derivative IX only could be isolated.