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Issue 10, 2019
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A retro Baeyer–Villiger reaction: electrochemical reduction of [60]fullerene-fused lactones to [60]fullerene-fused ketones

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Abstract

A highly efficient electrochemical reduction of [60]fullerene-fused lactones to [60]fullerene-fused ketones, a formal process of retro Baeyer–Villiger reaction, has been achieved for the first time. The electrochemically generated dianionic [60]fullerene-fused lactones can be transformed into [60]fullerene-fused ketones in the presence of acetic acid in 85–91% yields. Control experiments have been performed to elucidate the reaction mechanism. The products have been characterized with spectroscopic data and single-crystal X-ray analysis. Moreover, the electrochemical properties have also been investigated.

Graphical abstract: A retro Baeyer–Villiger reaction: electrochemical reduction of [60]fullerene-fused lactones to [60]fullerene-fused ketones

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Publication details

The article was received on 14 Nov 2018, accepted on 15 Jan 2019 and first published on 16 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC05089A
Citation: Chem. Sci., 2019,10, 3012-3017
  • Open access: Creative Commons BY license
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    A retro Baeyer–Villiger reaction: electrochemical reduction of [60]fullerene-fused lactones to [60]fullerene-fused ketones

    C. Niu, D. Zhou, Y. Yang, Z. Yin and G. Wang, Chem. Sci., 2019, 10, 3012
    DOI: 10.1039/C8SC05089A

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