Site-selective unidirectional benzylic sp(3) C–H oxidation of dodecahydrotriphenylene with RuCl(3)–NaIO(4): formation of benzylic ketones

Dodecahydrotriphenylene, a higher homologue of trindane chemoselectively undergoes unidirectional benzylic sp(3) C–H oxidation and the central benzene ring remains intact unlike that in trindane under similar reaction conditions. RuO(4) which generally attacks sp(2) C–H to form oxidative products is found to give benzylic ketones via sp(3) 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.