Highly selective N- and O-functionalization of adamantane utilizing nitrogen oxides. Kyodai-nitration of aliphatic hydrocarbons

In the presence of ozone at -78 degrees C, nitrogen dioxide selectively reacts rapidly with adamantane at the bridgehead position to give the corresponding nitration product, while in the presence of methanesulfonic acid at 0 degrees C, dinitrogen pentoxide readily reacts with this hydrocarbon at the same position exclusively to afford the corresponding nitrooxylation product, the yields of both products being quite satisfactory.