94238-10-5Relevant academic research and scientific papers
Chemoselectivity of Nitroxylation of Cage Hydrocarbons
Ivleva, E. A.,Klimochkin, Yu. N.,Leonova, M. V.
, p. 1702 - 1710 (2020/12/01)
Abstract: The composition of reaction mixtures obtained by nitroxylation of 13 cage hydrocarbons with 100% nitric acid and its mixtures with acetic acid, acetic anhydride, and methylene chloride has been studied. More reactive substrates react with lowest
Ozone-mediated nitration of adamantane and derivatives with nitrogen dioxide: Selectivity in the hydrogen abstraction by nitrogen trioxide and subsequent coupling of the resulting carbon radicals with nitrogen dioxide
Suzuki, Hitomi,Nonoyama, Nobuaki
, p. 2965 - 2971 (2007/10/03)
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- and O-functionalized products. The results may be rationalized in terms of the initial hydrogen abstraction by nitrogen trioxide, followed by rapid trapping of the resulting adamantyl radicals with nitrogen dioxide.
Reactions of 1- and 2-Adamantyl Radicals with Nitrogen Dioxide
Barabanova,Medzhinskii,Golod
, p. 1079 - 1082 (2007/10/03)
1- and 2-Adamantyl radicals similarly react with excess nitrogen dioxide to form respectively 1-nitro and 1-nitroxyadamane, 2-nitro and 2-nitroxyadamane, which are further nitrated to 1,3-dinitroadamantane, 1-nitro-3-nitroxyadamantane, 1,4-dinitroadamantane, and 1-nitro-4-nitroxyadamantane.
