Oxidative deamination of azafulleroids into C60 by peracids.

Org Biomol Chem

Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

Published: May 2015

Oxidation of azafulleroids with peracids regenerated C60 depending on the N-substituents. Alkyl-substituted azafulleroids preferred the oxidation of nitrogen to afford N-oxides as possible intermediates for C60 in moderate yields. Phenyl- and tosyl-substituted azafulleroids rather allowed the oxidation at the carbon cage. Theoretical calculations predicted the order of reactivity of azafulleroids as well as the relative N/C nucleophilicity.

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http://dx.doi.org/10.1039/c5ob00272aDOI Listing

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