Collect. Czech. Chem. Commun. 1986, 51, 1086-1093

Reaction of hydroxydiamantanes with chloroethylenes in sulfuric acid

Luděk Vodička, Jiří Burkhard and Josef Janků

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


Reaction of hydroxydiamantanes with 1,1-dichloroethylene in concentrated sulfuric acid leads to complex reaction mixtures, containing predominantly diamantylacetic and diamantanebisacetic acids. The same reaction with trichloroethylene affords diamantylchloroacetic and diamantanebischloroacetic acids. In all these products the substituents are bonded to the apical and secondary carbon atoms of the diamantane skeleton. For steric reason, acids with carboxyl in the medial position are not formed.