The Bingel monoadducts of La@C82: synthesis, characterization, and electrochemistry

Chemistry : a European Journal
Lai FengShigeru Nagase

Abstract

The reaction of La@C82 with diethyl bromomalonate in the presence of base (the Bingel reaction) generated five monoadducts which have been fully characterized. It was found that four of them (mono-A, -B, -C, and -D) are ESR-inactive, suggesting singly bonded regioisomers. In contrast, the fifth product (mono-E) is ESR-active, indicating that it possesses a cyclic moiety between the appended malonate group and the fullerene cage, analogous to conventional Bingel adducts. The differences in the molecular structures of mono-A, -B, -C, and -E result in varying thermal stabilities and electrochemical behavior. In particular, the singly bonded monoadducts undergo the retro-Bingel reaction either under thermal treatment or during electron transfer on the cyclic voltammetric timescale. However, mono-E shows remarkable thermal stability and perfect reversibility under the same experimental conditions.

References

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Citations

Aug 19, 2016·The Journal of Organic Chemistry·Pei ZhaoMasahiro Ehara
Mar 19, 2016·Chemistry : a European Journal·Juan Pablo MartínezMiquel Solà
Mar 22, 2016·Physical Chemistry Chemical Physics : PCCP·Pei ZhaoXiang Zhao
Oct 10, 2013·Angewandte Chemie·Marta IzquierdoLuis Echegoyen
Sep 25, 2009·Angewandte Chemie·Manuel N ChaurLuis Echegoyen
Apr 11, 2012·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Takeshi Akasaka, Xing Lu
Aug 16, 2014·Chemical Communications : Chem Comm·Xing LuShigeru Nagase
Nov 27, 2010·Physical Chemistry Chemical Physics : PCCP·Sílvia OsunaMiquel Solà
Mar 26, 2011·Chemical Communications : Chem Comm·Xing LuShigeru Nagase
Aug 22, 2012·Chemical Society Reviews·Xing LuShigeru Nagase
Apr 9, 2010·Journal of the American Chemical Society·Xing LuShigeru Nagase
Nov 13, 2008·Journal of the American Chemical Society·Yuta TakanoShigeru Nagase
Sep 5, 2009·Accounts of Chemical Research·Michio YamadaShigeru Nagase
Aug 24, 2012·Journal of the American Chemical Society·Makoto HachiyaTakeshi Akasaka
May 3, 2013·Chemical Reviews·Alexey A PopovLothar Dunsch

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