58652-35-0Relevant academic research and scientific papers
Nitration of adamantane and diamantane with nitronium tetrafluoroborate
Olah, George A.,Ramaiah, Pichika,Rao, Chandra B.,Sandford, Graham,Golam, Rasul,Trivedi, Nirupam J.,Olah, Judith A.
, p. 7246 - 7249 (2007/10/02)
The slow reaction of adamantane with nitronium tetrafluoroborate at room temperature in purified, nitrile-free nitromethane or in nitroethane gives 1-nitroadamantane in 66% and 74% isolated yield, respectively. Similar reaction of diamantane gives 62% 1-and 5% 4-nitrodiamantane. Initial reaction upon aqueous workup gives 1-adamantanol with 1-fluoroadamantane, 3-fluoro-1-adamantanol, and adamantanone as byproducts. Upon prolonged reaction 1-nitroadamantane is formed in good yield. The experimental data are in accord with intermediate formation of the 1-adamantyl cation (by hydride abstraction or cleavage of initially formed 1-nitroadamantane) followed by reaction with HNO2 or NO2-formed in the reaction, giving 1-adamantyl nitrite, which then undergoes cleavage-rearrangement to give 1-nitroadamantane. A small kinetic hydrogen isotope effect of kH/kD = 1.2-1.3 is indicative of a nonlinear highly unsymmetrical transition state in the rate-determining step of the reaction.
Fluorination of Adamantane Derivatives with Oxygen Difluoride
Bolte, Gerd,Haas, Alois
, p. 1982 - 1986 (2007/10/02)
Fluorination of adamantane and adamantane derivatives 1 with OF2 in the absence of an HF-trap gives fluoroadamantanes 2 and adamantanols 3 in varying amounts.Increasing yields of 2 are obtained in the presence of Na2CO3 as an HF-trap.In addition, the fluorooxahomoadamantanes 4b and e are formed in this reaction.The fluorination of adamantanone (5) with OF2 leads to analogous products.
