title: Highly efficient retro-cycloaddition reaction of isoxazolino[4,5:1,2][60]- and -[70]fullerenes.
abstract: Isoxazolino[4,5:1,2][60]- and -[70]fullerenes undergo an efficient retro-cycloaddition reaction to pristine fullerene by thermal treatment in the presence of an excess of a dienophile and Cu(II) catalysis, which can be selectively used in the presence of malonate or pyrrolidine cycloadducts. Trapping experiments using N-phenylmaleimide as dipolarophile have shown that the reaction mechanism occurs by thermal removal of the nitrile oxide 1,3-dipole, in a process which is favored by the presence of Cu(II) as the catalyst. The ESI-MS study supports the observed retro-cycloaddition process for both C60 and C70 derivatives. In contrast to previous electrochemical retro-cycloaddition processes observed in fulleropyrrolidines, isoxazolinofullerenes were stable under oxidative conditions.
authors: Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense, E-28040 Madrid, Spain. nazmar@quim.ucm.es
authors: Nazario
authors: N
authors: Martín
authors: Margarita
authors: M
authors: Altable
authors: Salvatore
authors: S
authors: Filippone
authors: Angel
authors: A
authors: Martín-Domenech
authors: Roberto
authors: R
authors: Martínez-Alvarez
authors: Margarita
authors: M
authors: Suarez
authors: Marta E
authors: ME
authors: Plonska-Brzezinska
authors: Olena
authors: O
authors: Lukoyanova
authors: Luis
authors: L
authors: Echegoyen