L. Cermenati, D. Dondi, M. Fagnoni
Aug 18, 2003
Citations
0
Influential Citations
38
Citations
Journal
Tetrahedron
Abstract
Abstract 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 + 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.