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

ABSTRACT: 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.

SUBMITTER: Bhatt GJ 

PROVIDER: S-EPMC9042685 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature