Synthesis of Oxosumanenes through Benzylic Oxidation

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 trimethylat...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-10, Vol.76 (19), p.8049-8052
Main Authors: Amaya, Toru, Hifumi, Maiko, Okada, Michiaki, Shimizu, Yasutomo, Moriuchi, Toshiyuki, Segawa, Kouji, Ando, Yoichi, Hirao, Toshikazu
Format: Article
Language:English
Subjects:
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo2012412