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Martín Doménech, A.6
Martín, N.7
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34248584021
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(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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Martín, N.1
Altable, M.2
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Martínez-Alvarez, R.5
Suarez, M.6
Plonska-Brzezinska, M.E.7
Lukoyanova, O.8
Echegoyen, L.9
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(b) Da Ros, T.; Prato, M.; Novello, F.; Maggini, M.; De Amici, M.; De Micheli, C. Chem. Commun. 1997, 59.
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(c) Da Ros, T.; Prato, M.; Lucchini, V. J. Org. Chem. 2000, 65, 4289.
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Delgado, J. L.; Oswald, F.; Cardinali, F.; Langa, F.; Martín, N. J. Org. Chem. 2008, 73 (8), 3184.
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Oswald, F.2
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Espíldora, E.; Delgado, J. L.; de la Cruz, P.; de la Hoz, A.; López-Arza, V.; Langa, F. Tetrahedron 2002, 58, 5821.
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Langa, F.6
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8
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61349151539
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Crystal data: C68H5N3O 3·L5(C6H5Cl, Mr, 1080.07, red thin plate (0.6 × 0.6 × 0.04 mm3, triclinic, space group P-1, a, 9.9093(8) A, b, 10.0293(8) Å, c, 24.979(2) Å, α, 80.616(2)°, β, 85.699(1)°, γ, 62.232(1)°, V, 2167.2(3) Å3, Z, 2, pcalcd, 1.655 g cm-3, F(000, 1089, μ, 0.191 mm-1, 2θmax, 50.0°, T, 296(2) K, 7567 unique reflections [R(int, 0.1106, R1, 0.0510, wR2, 0.1454 (all data, GOF(F2, 0.957, N0/NV, 7567/769, highest residual electron density 1.289 e Å-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 m
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-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).
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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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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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57249093639
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For a review, see
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(c) Mahapatra, S.; Halfen, J. A.; Tolman, W. B. J. Am. Chem. Soc. 1996, 118, 11575.
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Oxidations in Organic Chemistry
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(a) Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph 186; American Chemical Society: Washington, DC, 1990.
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(b) Alvarez, L. X; Lorraine, C. M.; Sorokin, B. Appl. Catal., A 2007, 325, 303.
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