title: Bisaziridine tetracarboxylates as building blocks in the stereoselective synthesis of C60-fullerene diads and dumbbell-like bis-C60-fullerene triads.
abstract: The synthesis of alkoxycarbonyl-substituted bisaziridines with the two aziridine units connected by conjugated p-phenylene, partly conjugated 1,1'-biphenyl-4,4'-diyl, and nonconjugated 4,4'-methylenediphenyl linkers was developed. The reaction of azomethine ylides derived from the bisaziridines with fullerene C(60) was optimized and used for the stereoselective preparation of both the monoadducts (C(60)-linker-aziridine dicarboxylate), and the dumbbell bisadducts (C(60)-linker-C(60)). The reasons for the observed selectivity of the azomethine ylide formation and cycloaddition were theoretically studied at the DFT B3LYP/6-31G(d) level or at the ONIOM B3LYP/6-31G(d):B3LYP/STO-3G level for fullerene-containing molecules.
authors.affiliation: Department of Chemistry, Saint Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, Russia.
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Konev
authors.forename: Alexander F
authors.initials: AF
authors.lastname: Khlebnikov
authors.forename: Holm
authors.initials: H
authors.lastname: Frauendorf