Collect. Czech. Chem. Commun. 1987, 52, 2028-2034

Reaction of adamantanone, diamantanone, and their derivatives with thionyl chloride

Josef Janků, Jiří Burkhard and Luděk Vodička

Laboratory of Synthetic Fuels, Prague Institute of Chemical Technology, 166 28 Prague 6


In reaction of adamantanone, diamantanone, and their chloro or oxo derivatives with thionyl chloride the oxo group is replaced with two chlorine atoms under formation of geminal dichloro derivatives. The presence of a chlorine atom or an oxo group in both ketones reduces the reaction rate. The reaction rate decreases with decreasing distance between the substituent and the carbonyl group. Ketones with chlorine atom in α- or β-axial position do not react with thionyl chloride. The reaction is accelerated by hydrogen chloride whereas in the presence of pyridine no reaction was observed.