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Fujiwara K, Komatsu K, Wang GW, et al. Derivatization of fullerene dimer C120 by the Bingel reaction and a 3He NMR study of 3He@C120 monoadducts. J Am Chem Soc. 2001;123(43):10715-20doi: 10.1021/ja011181n.
Fujiwara, K., Komatsu, K., Wang, G. W., Tanaka, T., Hirata, K., Yamamoto, K., & Saunders, M. (2001). Derivatization of fullerene dimer C120 by the Bingel reaction and a 3He NMR study of 3He@C120 monoadducts. Journal of the American Chemical Society, 123(43), 10715-20. https://doi.org/10.1021/ja011181n
Fujiwara, K, et al. "Derivatization of fullerene dimer C120 by the Bingel reaction and a 3He NMR study of 3He@C120 monoadducts." Journal of the American Chemical Society vol. 123,43 (2001): 10715-20. doi: https://doi.org/10.1021/ja011181n
Fujiwara K, Komatsu K, Wang GW, Tanaka T, Hirata K, Yamamoto K, Saunders M. Derivatization of fullerene dimer C120 by the Bingel reaction and a 3He NMR study of 3He@C120 monoadducts. J Am Chem Soc. 2001 Oct 31;123(43):10715-20. doi: 10.1021/ja011181n. PMID: 11674004.
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J Am Chem Soc. 2001 Oct 31;123(43):10715-20. doi: 10.1021/ja011181n.

Derivatization of fullerene dimer C120 by the Bingel reaction and a 3He NMR study of 3He@C120 monoadducts.

Journal of the American Chemical Society

K Fujiwara, K Komatsu, G W Wang, T Tanaka, K Hirata, K Yamamoto, M Saunders

Affiliations

  1. Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.

PMID: 11674004 DOI: 10.1021/ja011181n

Abstract

Cyclopropanation with diethyl bromomalonate and base (the Bingel reaction) was conducted on fullerene dimer C120 to give a mixture of "monoadducts" (45% yield) and "bisadducts" (< or =37% yield), while 18% of the C120 remained unchanged. The "monoadducts" were separated into five positional isomers, i.e., e(face), e(edge), trans-4, trans-3, and trans-2, by preparative HPLC. Assignments were made based on 1H (and 13C) NMR and confirmed by theoretical calculations of the addends' 1H NMR chemical shifts. The relative yields of these isomers were in fair agreement with those observed for the Bingel bisaddition of C60. The Bingel reaction was also carried out on the dimer C120 encapsulating 3He in one of the C60 cages. Each positional isomer of the "monoadduct" exhibited a pair of 3He NMR signals corresponding to an isomer with functionalization on the 3He-containing cage and the other isomer with functionalization on the empty cage. Using the 3He NMR spectroscopy, a pair of signals for the trans-1 isomer, which eluded detection by 1H NMR, were observed, in addition to pairs of signals for e(face), e(edge), trans-4, trans-3, and trans-2 isomers. The 3He NMR signals for isomers with functionalization on the 3He-containing cage were spread out over a 1.82-ppm range reflecting the direct effects of the addition pattern on the C60 surface. In contrast, the isomers with functionalization on the empty cage exhibited 3He NMR signals that appeared over a 0.14-ppm range, which was shown to be primarily due to changes in the diamagnetism of the functionalized cage based on theoretical calculations of 3He NMR chemical shifts for the model system in which the C60 cage encapsulating 3He was removed.

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