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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Construction of a hemifullerene skeleton: a regioselective intramolecular oxidative cyclization
Toru Amaya1, Takanori Ito, Toshikazu Hirao
1Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka 565-0871(Japan). amaya@chem.eng.osaka-u.ac.jp.
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.
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