Reaction of nitroso chlorides of the adamantane series with nucleophiles

Reactions of nitroso chlorides of 2-alkylydene adamantanes with O- and N-nucleophiles resulted in α-substituted oximes of the adamantane series. Reaction involved 1,4-nucleophilic addition of the nucleophiles to the generated in situ nitroso alkenes acting as the Michael acceptors. Reduction of the precursors of nitroso alkenes with sodium cyanoborohydride gave 2-substituted adamantylated oximes.