Issue 18, 2020

Kinetic investigation of the cyclopropanation process of fullerene C60 by halogenmethyl ketones under the conditions of the Bingel reaction

Abstract

The kinetics of the Bingel reaction with halogenmethyl ketones and C60 fullerene has been studied in streaming mode by sampling the reaction mixture at different time intervals and separating the components using HPLC. A quantum-chemical simulation of this cyclopropanation process has been carried out with the DFT method. The activation parameters of the cycloaddition process were determined theoretically and experimentally and correlated with each other. It has been revealed that the use of chloromethyl ketone as the cyclopropanation agent is preferable to its brominated analogue, and a two-fold excess of the substrate with respect to fullerene is the best option for the selective synthesis of mono-adducts.

Graphical abstract: Kinetic investigation of the cyclopropanation process of fullerene C60 by halogenmethyl ketones under the conditions of the Bingel reaction

Supplementary files

Article information

Article type
Paper
Submitted
21 Dec 2019
Accepted
04 Mar 2020
First published
30 Mar 2020

New J. Chem., 2020,44, 7277-7285

Kinetic investigation of the cyclopropanation process of fullerene C60 by halogenmethyl ketones under the conditions of the Bingel reaction

Y. N. Biglova, I. M. Sakhautdinov, R. N. Garifullin, G. F. Sakhautdinova and A. G. Mustafin, New J. Chem., 2020, 44, 7277 DOI: 10.1039/C9NJ06326A

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