Bingel reaction

What is Bingel reaction?

The Bingel reaction, which involves nucleophilic cyclopropanation with 2-halomalonates, is widely used as a method for functionalization/derivatization fullerenes.

Bingel reaction
Bingel reaction
Bingel reaction
Bingel reaction

Additionally, research has been conducted on the retro-Bingel reaction.

The functionalization of methanofullerenes through the Bingel reaction can be enhanced by employing a double Bingel reaction using bismalonates tethered with compounds such as Tröger base, [9,10]anthraceno bridges, isoxazolines, and others. This technique is a prime example of tether-directed remote functionalization.

Bingel reaction
Bingel reaction

Under base-catalyzed conditions, 1,3-disubstituted isobenzofurans produced from 1,4-disubstituted-1,4-epoxynaphthalenes and tetrazines can react with C60 to form corresponding Diels-Alder adducts, leading to the opening of a large orifice on the fullerene framework.

References

Bingel, C. (1993), Cyclopropanierung von Fullerenen. [Cyclopropanation of fullerenes.] Chem. Ber., 126: 1957-1959. https://doi.org/10.1002/cber.19931260829

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