Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C₆₀.

ABSTRACT: In this study, β-keto esters as readily available bio-based building blocks were used to decorate the C₆₀ sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel-Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C₆₀ fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C₆₀ derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and

SUBMITTER: Jaksic J 

PROVIDER: S-EPMC9040907 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature