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Construction of a Hemifullerene Skeleton: A Regioselective Intramolecular Oxidative Cyclization
Authors:Dr Toru Amaya  Takanori Ito  Prof?Dr Toshikazu Hirao
Institution:1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada‐oka, Suita, Osaka 565‐0871(Japan);2. JST, ACT‐C, 4‐1‐8 Honcho, Kawaguchi, Saitama, 332‐0012 (Japan)
Abstract:A two‐step synthesis of a strained π bowl, with hemifullerene skeleton from sumanene, was achieved in a high yield. The first step is a base‐promoted condensation reaction with a benzophenone compound, bis(3,5‐dimethylphenyl)methanone. The second step is the regioselective intramolecular oxidative cyclization, which is a key reaction for the hemifullerene skeleton synthesis. This regioselective cyclization is likely to be under thermodynamic control. This strategy will allow facile synthesis of various highly strained π bowls.
Keywords:arenes  fullerenes  fused‐ring system  regioselectivity
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