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Construction of a Hemifullerene Skeleton: A Regioselective Intramolecular Oxidative Cyclization
Author(s) -
Amaya Toru,
Ito Takanori,
Hirao Toshikazu
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500548
Subject(s) - regioselectivity , intramolecular force , chemistry , benzophenone , skeleton (computer programming) , oxidative phosphorylation , yield (engineering) , combinatorial chemistry , condensation , stereochemistry , photochemistry , organic chemistry , catalysis , materials science , biochemistry , computer science , metallurgy , programming language , physics , thermodynamics
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.