TiO2 photocatalysis of adamantane in oxygen equilibrated MeCN yields 1- and 2-adamantanol and adamantanone with limited degradation and preference for functionalization at the 1 position, particularly in the presence of silver salts. Oxidation in CH2Cl2 is less selective. The oxidation of cyclohexane and cyclododecane is slower. In N2-flushed solutions with Agþ as a sacrificial acceptor, products from the trapping of both 1-adamantyl radical (adamantyl methyl ketone) and cation (N-adamantylacetamide) are obtained. Furthermore, alkylation of an electrophilic alkene (isopropylydenmalononitrile) has been obtained, though in a low yield.
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