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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...

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Bibliographic Details
Published in:RSC advances 2021-10, Vol.11 (55), p.34498-34502
Main Authors: Bhatt, Gaurang J, Deota, Pradeep T, Upadhyay, Deepak, Jha, Prafulla K
Format: Article
Language:English
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Summary: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.
ISSN:2046-2069
DOI:10.1039/d1ra06897k