Abstract
Oxygenation reactions of adamantanes with ferrous iron-molecular oxygen in phosphate buffer were investigated and the structures of the products were elucidated. In the reaction of adamantane-1-acetic acid (1a), five oxygenated products, the C (2)-oxo, C (4)-oxo, C (2), C (6)-dioxo, C (4)-ol, and C (3)-ol derivatives, were obtained. Similar oxygenation also occurred in the reaction of adamantane-1-carboxylic acid (2a) to give three products, the C (4)-oxo, C (4)-ol, and C (3)-ol derivatives. The oxy-functionalization of 1a and 2a in 0.5M phosphate buffer (pH 6.8) was found to occur almost quantitatively on addition of an appropriate amount of ferrous iron.
