Reaction of 5-oxo-4-oxahomoadamantane with thionyl chloride

On reaction with thionyl chloride 5-oxo-4-oxahomoadamantane gives rise to a mixture of 4 a -chloro- and 4 e -chloro-2-adamantanone. The carbonyl group of chloroadamantane further reacts with thionyl chloride under formation of 2,2,4 e -trichloroadamantane. In the same way adamantanone reacts with thionyl chloride, giving rise to 2,2-dichloroadamantane.