Titanium dioxide photocatalysis of adamantane

✍ Scribed by Laura Cermenati; Daniele Dondi; Maurizio Fagnoni; Angelo Albini

• Book ID: 104205650
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 149 KB
• Volume: 59
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(03)01092-5

✦ Synopsis

TiO 2 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 CH 2 Cl 2 is less selective. The oxidation of cyclohexane and cyclododecane is slower. In N 2 -flushed solutions with Ag þ 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.