160558-58-7Relevant articles and documents
Electron-acceptor-induced isomerization of aryl [6,5] open fulleroids to [6,6] closed methanofullerenes and the electrochemical evaluation of their free energy difference
Hall, Melvin H.,Shevlin, Philip,Lu, Huajun,Gichuhi, Anthony,Shannon, Curtis
, p. 3357 - 3363 (2006)
The thermal and photochemical rearrangements of a series of aryl substituted [6,5] open fulleroids to [6,6] closed methanofullerenes are accelerated in the presence in of electron acceptors. These [6,5] open fulleroids, facilitated by electron acceptors, rearrange thermally by a zwitteronic-type intermediate, while the photochemical reactions proceed via an excited-state electron-transfer process. The oxidation potentials of these [6,5] open fulleroids and their corresponding [6,6] closed methanofullerenes isomers have been evaluated. The free energy difference between the [6,5] open fulleroids and their corresponding [6,6] closed isomers have been estimated from the difference in their oxidation potentials.
Bis(4-methoxyphenyl)methano[60]fullerene with a methano bridge at the 6-6-ring junction
Tezuka, Yoshihiko,Kawasaki, Nobuyuki,Yajima, Hirofumi,Ishii, Tadahiro,Oyama, Toshiyuki,Takeuchi, Kazuo,Nakao, Akiko,Katayama, Chuji
, p. 1008 - 1010 (1996)
In the title compound, C75H14O2, a bis(4-methoxyphenyl)methylene group bridges a 6-6-ring junction of the C60 sphere, forming a slightly deformed cyclopropane ring. The C-C bond length involved in the cyclopropane ring fusion is 1.635 (4) A, more than 0.2 A longer than that at the 6-6-ring junction of C60. The elongation of this C-C bond leads to a slight deformation of the C60 framework, especially a shortening of two C-C bonds in equatorial positions.
Selective electrolytic removal of bis(alkoxycarbonyl)methano addends from C60 bis-adducts and electrochemical stability of C70 derivatives
Kessinger, Roland,Fender, Nicolette S.,Echegoyen, Lourdes E.,Thilgen, Carlo,Echegoyen, Luis,Diederich, Francois
, p. 2184 - 2192 (2007/10/03)
The novel mixed his-adducts of C60, (±)-4-(±)-8 and 9, with a bis(ethoxycarbonyl)methano addend (Bingel addend) and a second addend ([1,2]benzeno, but[2]eno, methaniminomethano, or diarylmethano) bridging 6,6-closed bonds of the carbon sphere were synthesized in two-step reactions. Each bis-adduct was exhaustively electrolyzed at the potential of the second fullerene-centered reduction step, resulting in the selective removal of the Bingel addend (retro-Bingel reaction) to produce the corresponding mono-adducts, which were isolated in yields of over 60%. These results open up the possibility of using the Bingel addend as a temporary protecting and directing group in the construction of multiple adducts of C60 with unusual addition patterns. The Bingel-type mono-adduct of C70 10 and the constitutionally isomeric bis-adducts 11, (±)-12, and (±)-13 were also included in this investigation. A large difference in the electrochemical behavior between C70, bis-adducts and the corresponding C60 derivatives was observed. Thus, the intramolecular "walk-on-the-sphere" isomerization which occurs readily with Bingel-type bis-adducts of C60 under the conditions of two-electron controlled potential electrolysis (CPE) is only a minor reaction pathway in the series of C70 derivatives. The latter preferentially undergo retro-Bingel reaction.
