Collect. Czech. Chem. Commun. 1984, 49, 1900-1906

Synthesis and reactions of hydroxydiamantanones

Luděk Vodičkaa, Sergei D. Isaevb, Jiří Burkharda and Josef Jankůa

a Laboratory of Synthetic Fuels, Prague Institute of Chemical Technology, 166 28 Prague 6
b Department of Organic Chemistry, Kiev Polytechnical Institute, Kiev, USSR


Diamantanone can be oxidized with chromium trioxide in acetic acid solutions to give 11-hydroxy-, 1-hydroxy-, and 9-hydroxy-3-diamantanone as the major products and two diamantanonediones of unelucidated structure as by-products. The Koch-Haaf carboxylation of hydroxydiamantanones results in the formation of the corresponding oxodiamantanecarboxylic acids. Reacted with 100% HNO3, diamantanone transforms into 9-(3-diamantanoyl) nitrate. Reactions of the carbonyl groups of these compounds with H2NOSO2OH lead to hydrazidiamantane derivatives, which oxidized with CrO3 provide the azidiamantane derivatives.