Synthesis and Reactions of 2-Adamantylidenenitromethane
Synthesis of 2-adamantylidenenitromethane by nitration of 2-methyl-2-adamantanol was developed. Reaction of the 2-adamantylidenenitromethane with acids HX (X = ONO2, Cl, Br) yields the corresponding 2-X-adamantane-2-carboxylic acids, and under conditions of Ritter's reaction affords 2-acetylaminoadamantane-2-carboxylic acid. Reaction of the 2-adamantylidenenitromethane with nitric acid in a mixture with acetic anhydride occurs with carcass rearrangement and results in 4-exo-nitroxy-3-protoadamantanecarboxylic acid. The reduction of the nitroolefin with lithium aluminum hydride furnishes 2-aminomethyladamantane, and reaction with excess methylmagnesium iodide gives N-(2-methyl-2-adamantyl)methyl-N-hydroxylamine.
Klimochkin,Leonova,Moiseev
p. 494 - 498
(2007/10/03)
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