Premium
The Bingel Monoadducts of La@C 82 : Synthesis, Characterization, and Electrochemistry
Author(s) -
Feng Lai,
Wakahara Takatsugu,
Nakahodo Tsukasa,
Tsuchiya Takahiro,
Piao Qiuyue,
Maeda Yutaka,
Lian Yongfu,
Akasaka Takeshi,
Horn Ernst,
Yoza Kenji,
Kato Tatsuhisa,
Mizorogi Naomi,
Nagase Shigeru
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501545
Subject(s) - moiety , adduct , electrochemistry , chemistry , diethyl malonate , thermal stability , malonate , fullerene , stereochemistry , organic chemistry , electrode , catalysis
The reaction of La@C 82 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.