66633-37-2Relevant academic research and scientific papers
Transformations of 2-Alkyl-2-adamantanols in Nitric Acid
Klimochkin,Leonova,Moiseev
, p. 34 - 39 (2007/10/03)
2-Methyl-2-adamantanol reacts with a mixture of nitric acid and acetic anhydride to afford a number of products: 2-methyl-2-nitroxyadamantane, 2-adamantanone, 2-adamantylidenenitromethane, and products formed by stabilization of 2-nitromethyl-2-adamantyl cation. The reaction of 2-ethyl-2-adamantanol with the same reagent yields a mixture of compounds from which 2-adamantanone, 2-(1-acetoxyethyl)-2-adamantanol, and products of stabilization of 2-(1-nitroethyl)-2-adamantyl cation were isolated. The reaction of 2-isopropyl-2-adamantanol with HNO3-Ac2O is accompanied by rearrangement of the isopropyl moiety via 1,2-alkyl shift to give methyl 2-methyl-2-adamantyl ketone.
