Method for Producing Substituted Diamantanes

Abstract

The invention at hand provides at least dinitroxylated diamantanes. In addition, it provides methods for producing substituted diamantanes with high yields and selectivity. According to the invention, dinitroxylated diamantanes are suitable for being reacted with nucleophiles to form the corresponding disubstituted diamantanes. Surprisingly, it was discovered that at least dinitroxylated or hydroxylated diamantanes are rearranged in the presence of a strong acid, creating at least 4,9-nitroxylated or hydroxylated diamantanes. On the basis of this, 4,9-substituted diamantanes are able to be produced in a targeted manner by reaction with further nucleophiles. Thus, the invention at hand provides the following methods according to the present invention for producing at least disubstituted diamantanes: a) at least dinitroxylation, followed by the substitution of all nitroxy groups by a nucleophile or b) at least dinitroxylation, subsequent rearrangement in the presence of a strong acid, after realised rearrangement all nitroxy groups are replaced by a nucleophile or c) at least dinitroxylation, subsequent reaction with water (as nucleophile), rearrangement of the at least dihydroxylated compound in the presence of a strong acid, after realised rearrangement all hydroxy groups are replaced by another nucleophile.

Dependencies are inferred from the claim text.