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

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...

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Published inChemical science (Cambridge) Vol. 10; no. 10; pp. 3012 - 3017
Main Authors Niu, Chuang, Zhou, Dian-Bing, Yang, Yong, Yin, Zheng-Chun, Wang, Guan-Wu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.03.2019
Royal Society of Chemistry
Subjects
Acetic acid
Chemical reduction
Chemistry
Chemistry, Multidisciplinary
Crystallography
Electrochemical analysis
Fullerenes
Ketones
Lactones
NMR
Nuclear magnetic resonance
Physical Sciences
Reaction mechanisms
Science & Technology
Single crystals
X ray analysis
FULLERENES
FUNCTIONALIZATION
REAGENTS
CHEMISTRY
C-60
REGIOSELECTIVE ELECTROSYNTHESIS
ORGANIC PHOTOVOLTAICS
WATER
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc05089a