Ozone-mediated nitration of adamantane and derivatives with nitrogen dioxide: selectivity in the hydrogen abstraction by nitrogen trioxide and subsequent coupling of …

H Suzuki, N Nonoyama

Index: Suzuki, Hitomi; Nonoyama, Nobuaki Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 20 p. 2965 - 2971

Full Text: HTML

Citation Number: 3

Abstract

In the presence of ozone at–78° C, nitrogen dioxide reacts rapidly and selectively with adamantane at a bridgehead position to give the corresponding nitro derivative as the sole major product. The relative reactivity has been determined for a series of 1-substituted adamantanes, which reveals that electron-withdrawing substituents exert a considerable influence on the ease of substitution at the γ-position as well as the distribution of the N- ...