Synthesis of oxosumanenes through benzylic oxidation.

J Org Chem

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka 565-0871, Japan.

Published: October 2011

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Article Abstract

Oxosumanenes were synthesized through benzylic oxidation. The electronic and redox properties were revealed to exhibit the expanded π-conjugation compared to sumanene. Single-crystal X-ray analysis of monooxosumanene showed columnar π-stacking in a concave-convex fashion. Stereoselective trimethylation of the trioxo derivative was performed via 1,2-addition to the carbonyl groups.

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http://dx.doi.org/10.1021/jo2012412DOI Listing

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