4.7 Article

Synthesis of Oxosumanenes through Benzylic Oxidation

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 19, Pages 8049-8052

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo2012412

Keywords

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Funding

  1. Japan Society for the Promotion of Science [22245007, 22685006]
  2. Japan Science and Technology Agency [AS2211281D]
  3. Nissan Science Foundation
  4. Grants-in-Aid for Scientific Research [22685006, 22245007] Funding Source: KAKEN

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Oxosumanenes were synthesized through benzylic oxidation. The electronic and redox properties were revealed to exhibit the expanded pi-conjugation compared to sumanene. Single-crystal X-ray analysis of monooxosumanene showed columnar pi-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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