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Open‐cage fullerenes with a 19‐membered orifice were prepared in three steps from C60. The key step for cage‐opening is aniline mediated ring expansion of a fullerene‐mixed peroxide with a ketolactone moiety on the orifice. Release of ring strain on the spherical fullerene cage served as the main driving force for the efficient cage‐opening sequence. Encapsulation of oxygen could be achieved at room temperature under moderate pressure (50 atm) and the encapsulated oxygen could be released slowly under ambient conditions. The activation energy of the oxygen‐releasing process is 18.8 kcal mol−1 and the half‐life at 37 °C was 73 min, which makes this open‐cage fullerene derivative a potential oxygen‐delivery material. [ABSTRACT FROM AUTHOR]

Abstract: An open‐cage C60 derivative 9 with anilino, hemiketal, and lactone moieties on the edge of the opening was prepared through a fullerene‐mixed peroxide procedure. Key steps include decarbonylation, intramolecular Friedel–Crafts reaction and oxetane ring opening rearrangement. The open‐cage compound 9 readily reacts with various metal salts. A nickel complex was obtained by treating 9 with NiCl2 at r.t. followed by purification on a silica gel column. Single‐crystal X‐ray diffraction analysis showed that the nickel ion is coordinated to two ligands with an octahedral geometry. [ABSTRACT FROM AUTHOR]

Wer wagt es, den Käfig zu öffnen? Das Azahomoazafulleren 1 wurde aus dem tert ‐ Butylperoxy ‐ substituierten Azafullerenderivat C59NBr(OOtBu)4 hergestellt. Die Addition von Singulett ‐ Sauerstoff an 1 führte zur Bildung des offenen Azafullerens 2 mit einer Ketoimidgruppe an der Öffnung. Das MALDI ‐ TOF ‐ Massenspektrum des Produkts der Hydrolyse von 1 enthält ein eindeutiges Signal für das Diazafulleren C58N2 (siehe Struktur 3). [ABSTRACT FROM AUTHOR]

Wer wagt es, den Käfig zu öffnen? Das Azahomoazafulleren 1 wurde aus dem tert ‐ Butylperoxy ‐ substituierten Azafullerenderivat C59NBr(OOtBu)4 hergestellt. Die Addition von Singulett ‐ Sauerstoff an 1 führte zur Bildung des offenen Azafullerens 2 mit einer Ketoimidgruppe an der Öffnung. Das MALDI ‐ TOF ‐ Massenspektrum des Produkts der Hydrolyse von 1 enthält ein eindeutiges Signal für das Diazafulleren C58N2 (siehe Struktur 3). [ABSTRACT FROM AUTHOR]

Abstract: The fullerendiol C60(OH)2(OOt-Bu)4 1 reacts with various arylboronic acids ArB(OH)2 to form fullerene-containing boronic esters C60(O2BAr)(OOt-Bu)4 in up to 95% yield depending on the structure of aryl group. Bis(pinacolato)diboron (B(OCMe2)2)2 also reacts with 1 to form C60(O2BB(OCMe2)2)(OOt-Bu)4. The bisboronic ester C60(O)(O2BAr)2(OOt-Bu)2 was also obtained starting from a tetrahydroxyl fullerene derivative C60(O)(OH)4(OOt-Bu)2. The fullerenyl boronic esters are moderately stable in air. Single crystal X-ray structure of C60(O2BPh)(OOt-Bu)4 was obtained. [Copyright &y& Elsevier]