Site-selective unidirectional benzylic sp3 C-H oxidation of dodecahydrotriphenylene with RuCl3-NaIO4: formation of benzylic ketones.

Dodecahydrotriphenylene, a higher homologue of trindane chemoselectively undergoes unidirectional benzylic sp3 C-H oxidation and the central benzene ring remains intact unlike that in trindane under similar reaction conditions. RuO4 which generally attacks sp2 C-H to form oxidative products is found to give benzylic ketones via sp3 C-H oxidation. Density functional theory (DFT) calculations have also been performed to analyse the potential energy, energy barrier and HOMO-LUMO energy gap of the products.