Oxidation of 3-alkyl-substituted 2-pyrazolino[60]fullerenes: A new formyl-containing building block for fullerene chemistry

Organic Letters

Volumn 10, Issue 17, 2008, Pages 3705-3708

  Delgado, Juan Luis ^a   Cardinali, François ^b   Espildora, Eva ^a   Torres, M Rosario ^a   Langa, Fernando ^b   Martín, Nazario ^a,c  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

^c INSTITUTO MADRILEÑO DE ESTUDIOS AVANZADOS EN NANOCIENCIA IMDEA NANOCIENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61349129082     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801308g     Document Type: Article

References (15)

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3. (a) Martín, N.; Altable, M.; Filippone, S.; Martín- Doménech, A.; Martínez-Alvarez, R.; Suarez, M.; Plonska-Brzezinska, M. E.; Lukoyanova, O.; Echegoyen, L. J. Org. Chem. 2007, 72, 3840.
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8. -3. X-ray diffraction data were measured on a Bruker Smart CCD diffractometer, with graphite-monochromated Mo-Kα radiation (λ = 0.71073 Å) operating at 50 kV and 35 mA. The intensity data were collected over a hemisphere of the reciprocal space by combination of three exposure sets. Each exposure of 20 s covered 0.3 in 01. Reflection range for the data collection were 1.65° < θ < 25.0°. The first 100 frames were recollected at the end of the data collection to monitor crystal decay, and no appreciable decay was observed. Structure solution and refinement: The structure was solved by direct methods. The refinement was done by full matrix least-squares procedures on F2 (SHELXTL version 5.1). The non-hydrogen atoms were refined anisotropically. All hydrogen atoms were calculated at their geometrical positions and refined as riding on their respective carbon atoms except H2 bonded to C2 atom (from formyl group) which was located from Fourier synthesis difference and the coordinates were refined. CCDC 687339 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving. html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax (+44)1223-336-033; or deposit@ ccdc.cam.ac.uk).
9. To shed light on the influence of the fullerene unit, we performed the same experiments on a similar 2-pyrazolino-based molecule, 3-methyl-1- phenylpyrazole without the fullerene moiety. TLC analysis of reaction of this compound with copper(II) triflate in o-DCB at reflux for 2 days revealed that this derivative does not undergo any oxidation process.
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