Reactivities of the prism-shaped diamondoids [1(2)3]tetramantane and [12312]hexamantane (cyclohexamantane).

Various functional groups have been incorporated into the structures of the naturally occurring diamondoids [1(2)3]tetramantane and [12312]hexamantane (cyclohexamantane), which represent hydrogen-terminated prism-shaped nanodiamonds. The selectivities of the C-H substitutions in [1(2)3]tetramantane depend on the reagent employed and give products substituted at either central (through bromination) or peripheral (through nitroxylation and photo-oxidation) positions. The hydrogen-coupled electron-transfer mechanism of C-H nitroxylation with the model electrophile NO(2)(+).