Chemical Communications

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

H Suzuki, N Nonoyama

Index: Suzuki, Hitomi; Nonoyama, Nobuaki Chemical Communications, 1996 , # 15 p. 1783 - 1784

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Abstract

In the presence of ozone at–78° 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° 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.