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Method for producing substituted diamantanes

25.06.2009
The invention at hand provides novel diamantanes not previously known which have been at least dinitroxylated. During the production of these compounds, at least one nitroxy group is bound to an apical carbon atom.<p>

The at least dinitroxylated diamantanes according to the present invention can easily be converted by acidic hydrolysis to the corresponding hydroxylated diamantanes.<p> Surprisingly, it has been found that dinitroxylated as well as dihydroxylated diamantanes are rearranged in the presence of a strong acid if one of the two nitroxy or hydroxy groups had been previously bound to an apical carbon atom. During this rearrangement, a nitroxy or hydroxy group which had not been previously bound to an apical carbon atom migrates to an apical carbon atom to which a hydrogen atom had been previously bound. The rearrangement product may subsequently react with further nucleophiles. Thereby, the invention at hand allows, for the first time, the selective production of diamantanes which have been at least diderivatized.

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