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

Chuang Niu; Dian-Bing Zhou; Yong Yang; Zheng-Chun Yin; Guan-Wu Wang

doi:10.1039/c8sc05089a

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

Chem Sci. 2019 Jan 16;10(10):3012-3017. doi: 10.1039/c8sc05089a. eCollection 2019 Mar 14.

Authors

Chuang Niu¹, Dian-Bing Zhou¹, Yong Yang¹, Zheng-Chun Yin¹, Guan-Wu Wang^{1

2}

Affiliations

¹ Hefei National Laboratory for Physical Sciences at Microscale , CAS Key Laboratory of Soft Matter Chemistry , iChEM (Collaborative Innovation Center of Chemistry for Energy Materials) , Center for Excellence in Molecular Synthesis of CAS , Department of Chemistry , University of Science and Technology of China , Hefei , Anhui 230026 , P. R. China . Email: gwang@ustc.edu.cn.
² State Key Laboratory of Applied Organic Chemistry , Lanzhou University , Lanzhou , Gansu 730000 , P. R. China.

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.