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
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.
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.
